15_page_[3] 5-'GH'-3-((4-'GH'piperazin-1-yl)methyl)-1H-indole [Reaxys, All Preps (199–276 of 276), S

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Citations (72)

References

199

Synthesize Find similar Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943704 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


200

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Rx-ID: 23883839 Find similar reactions

Merce-Vidal, Ramon; Andaluz-Mataro, Blas; Frigola-Constansa, Jordi

Patent: US2003/191124 A1, 2003 ; Title/Abstract Full Text Show Details

Compounds object of the present invention that correspond to the above formula can be selected from among ... [15] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]-4-phenylbenzenesulphonamide. [16] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]quinoline-8-sulphonamide. [17] N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide. [18] N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide [19] N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide.

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Merce-Vidal, Ramon; Andaluz-Mataro, Blas; Frigola-Constansa, Jordi

Patent: US2003/191124 A1, 2003 ; Title/Abstract Full Text Show Details

, selected from among the following group: ... [15] N-[3-(1-methylpiperdin-4-yl)-1H-indol-5-yl]-4-phenylbenzenesulphonamide. [16] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]quinoline-8-sulphonamide. [17] N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide. [18] N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide. [19] N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide.

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Laboratorios del Dr. Esteve S.A.

Patent: EP2018861 A1, 2009 ; Title/Abstract Full Text Show Details

It is further preferred if the compound binding to the 5HT6-receptor being used according to the invention is selected from the following group of sulfonamide compounds according to formula lba consisting of: ... [15] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]-4-phenylbenzenesulphonamide. [16] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]quinoline-8-sulphonamide. [17] N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide. [18] N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide. [19] N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide. Hide Details

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Laboratorios del Dr. Esteve S.A.

Patent: EP2018861 A1, 2009 ; Title/Abstract Full Text Show Details

Use according to claim 8, wherein the compound binding to the 5HT6-receptor is selected from the following group of sulfonamide compounds according to formula Iba consisting of: ... [15] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]-4-phenylbenzenesulphonamide. [16] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]quinoline-8-sulphonamide. [17] N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide. [18] N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide.


[19] N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide.

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Laboratorios del Dr. Esteve S.A.

Patent: EP2020230 A1, 2009 ; Title/Abstract Full Text Show Details

It is a further preferred embodiment of the combination of active substances according to the invention if the compound/s binding to the 5HT6-receptor according to formula (Iba) is/are selected from the following group of sulfonamide compounds consisting of: ... [15] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]-4-phenylbenzenesulphonamide. [16] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]quinoline-8-sulphonamide. [17] N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide. [18] N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide. [19] N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide.

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Laboratorios del Dr. Esteve S.A.

Patent: EP2020230 A1, 2009 ; Title/Abstract Full Text Show Details

A combination of active substances according to claim 14, wherein the compound/s binding to the 5HT6-receptor is/are selected from the following group of sulfonamide compounds according to formula (Iba) consisting of: ... [15] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]-4-phenylbenzenesulphonamide. [16] N-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]quinoline-8-sulphonamide. [17] N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide. [18] N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide. [19] N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide.

201

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Rx-ID: 32943569 Find similar reactions

202

Stage #1: formaldehyd; (2R,3R)-2(2,4-difluorophenyl)-3-(piperazin-1yl)-1-(1H-1,2,4-triazol-1-yl)butan-2ol With acetic acid in ethanol

T=0°C; 1 h; Stage #2: 1H-indole-5-carbonitrile in ethanol

T=0 - 40°C; 12 h;

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Synthesize Find similar

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943590 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

203

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Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943612 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

204

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Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C

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Rx-ID: 32943636 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


View Scheme

205

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Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943660 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

206

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207

Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943686 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


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Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943711 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

208

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Rx-ID: 32943568 Find similar reactions

209

Stage #1: formaldehyd; (2R,3R)-2(2,4-difluorophenyl)-3-(piperazin-1yl)-1-(1H-1,2,4-triazol-1-yl)butan-2ol With acetic acid in ethanol

T=0°C; 1 h; Stage #2: 5-Methoxy-1H-indole in ethanol

T=0 - 40°C; 12 h;

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Synthesize Find similar

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar

Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943588 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

210

Synthesize Find similar

Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943610 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

211

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Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C

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Rx-ID: 32943634 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


View Scheme

212

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Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943658 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

213

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214

Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943684 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


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Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943709 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

215

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Rx-ID: 23023108 Find similar reactions

XENOVA LIMITED

Patent: WO2004/65389 A1, 2004 ; Location in patent: Page 51 ;

Title/Abstract Full Text Show Details

216

Rx-ID: 32943575

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Synthesize Find similar


Find similar reactions

Stage #1: formaldehyd; (2R,3R)-2(2,4-difluorophenyl)-3-(piperazin-1yl)-1-(1H-1,2,4-triazol-1-yl)butan-2ol With acetic acid in ethanol

T=0°C; 1 h; Stage #2: 5-chloro-1H-indole in ethanol

T=0 - 40°C; 12 h;

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

217

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Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943584 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

218

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Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943606 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


219

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Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943630 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

220

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Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943654 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

221

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Synthesize Find similar

Rx-ID: 32943680 Find similar reactions


Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

222

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Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943705 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

223

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Rx-ID: 32943578 Find similar reactions

Stage #1: formaldehyd; (2R,3R)-2(2,4-difluorophenyl)-3-(piperazin-1yl)-1-(1H-1,2,4-triazol-1-yl)butan-2ol With acetic acid in ethanol

T=0°C; 1 h; Stage #2: 5-azido-1H-indole in ethanol

T=0 - 40°C; 12 h;

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Synthesize Find similar

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

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224

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Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943589 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

225

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226

Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943611 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


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Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943635 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

227

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Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943659 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

228

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Synthesize Find similar

Rx-ID: 32943685 Find similar reactions


Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

229

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Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943710 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

230

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Rx-ID: 29771462 Find similar reactions

MERCK SHARP andamp;; DOHME CORP.; STUMP, Craig, A.; QUIGLEY, Amy, G.; THEBERGE, Cory, R.; WOOD, Michael, R.

Patent: WO2010/107605 A1, 2010 ; Location in patent: Page/Page column 95; 97 ; Title/Abstract Full Text Show Details


231

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Rx-ID: 32943573 Find similar reactions

Stage #1: formaldehyd; (2R,3R)-2(2,4-difluorophenyl)-3-(piperazin-1yl)-1-(1H-1,2,4-triazol-1-yl)butan-2ol With acetic acid in ethanol

T=0°C; 1 h; Stage #2: 1H-indole-5carbaldehyde oxime in ethanol

T=0 - 40°C; 12 h;

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Synthesize Find similar

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

232

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233

Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943591 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar

Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943613 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

234

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Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943637 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

235

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Synthesize Find similar

Rx-ID: 32943661 Find similar reactions


Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

236

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Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943687 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

237

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Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943712 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


238

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Rx-ID: 32943576 Find similar reactions

Stage #1: formaldehyd; (2R,3R)-2(2,4-difluorophenyl)-3-(piperazin-1yl)-1-(1H-1,2,4-triazol-1-yl)butan-2ol With acetic acid in ethanol

T=0°C; 1 h; Stage #2: 5-Nitro-1H-indole in ethanol

T=0 - 40°C; 12 h;

Synthesize Find similar

Synthesize Find similar

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

239

Synthesize Find similar

240

Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943587 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar


Synthesize Find similar

Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943609 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

241

Synthesize Find similar

Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme

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Rx-ID: 32943633 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

242

Synthesize Find similar

Synthesize Find similar

Rx-ID: 32943657 Find similar reactions


Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

243

Synthesize Find similar

Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943683 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

244

Synthesize Find similar

Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943708 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


245

Synthesize Find similar

Multi-step reaction with 3 steps 1: acetic acid / 35 °C 2: palladium on activated carbon; hydrogen / ethanol / 6 h / 20 °C 3: methanol / Reflux View Scheme

Synthesize Find similar

Rx-ID: 46330279 Find similar reactions

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang

European Journal of Medicinal Chemistry, 2017 , vol. 139, p. 492 - 502 Title/Abstract Full Text View citing articles Show Details

246

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Multi-step reaction with 3 steps 1: acetic acid / 35 °C 2: palladium on activated carbon; hydrogen / ethanol / 6 h / 20 °C 3: methanol / Reflux View Scheme

Synthesize Find similar

Rx-ID: 46330358 Find similar reactions

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang

European Journal of Medicinal Chemistry, 2017 , vol. 139, p. 492 - 502 Title/Abstract Full Text View citing articles Show Details

247

Synthesize Find similar

Multi-step reaction with 2 steps 1: palladium on activated carbon; hydrogen / ethanol / 6 h / 20 °C 2: methanol / Reflux

Synthesize Find similar

Rx-ID: 46330381 Find similar reactions

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang

European Journal of Medicinal Chemistry, 2017 , vol. 139, p. 492 - 502 Title/Abstract Full Text View citing articles Show Details


View Scheme

248

Synthesize Find similar

Rx-ID: 46330393 Find similar reactions

50%

in methanol

Reflux; Hide Experimental Procedure

Synthesize Find similar

Synthesize Find similar

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang

European Journal of Medicinal Chemistry, 2017 , vol. 139, p. 492 - 502 Title/Abstract Full Text View citing articles Show Details

4.1.12. General procedure for preparation of compounds A1-A17

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

249

Synthesize Find similar

Rx-ID: 23341952 Find similar reactions

SUGEN, INC.

Patent: WO2004/76412 A2, 2004 ; Location in patent: Page 101; 140 ;

Title/Abstract Full Text Show Details

250

Synthesize Find similar

Rx-ID: 23341954 Find similar reactions


SUGEN, INC.

Patent: WO2004/76412 A2, 2004 ; Location in patent: Page 101; 140 ;

Title/Abstract Full Text Show Details

251

Synthesize Find similar

Rx-ID: 23342495 Find similar reactions

SUGEN, INC.

Patent: WO2004/76412 A2, 2004 ; Location in patent: Page 117; 217 ;

Title/Abstract Full Text Show Details

252

Synthesize Find similar

Rx-ID: 32943562 Find similar reactions

253

Stage #1: formaldehyd; (2R,3R)-2(2,4-difluorophenyl)-3-(piperazin-1yl)-1-(1H-1,2,4-triazol-1-yl)butan-2ol With acetic acid in ethanol

T=0°C; 1 h; Stage #2: 5-Bromo-1H-indole in ethanol

T=0 - 40°C; 12 h;

Synthesize Find similar

Synthesize Find similar

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar


Synthesize Find similar

Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943585 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

254

Synthesize Find similar

Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943607 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

255

Synthesize Find similar

Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943631 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


256

Synthesize Find similar

Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943655 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

257

Synthesize Find similar

258

Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943681 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details


Synthesize Find similar

Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme

Synthesize Find similar

Rx-ID: 32943706 Find similar reactions

Na, Young Min

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details

259

Synthesize Find similar

With methanol; sodium cyanoborohydride

T=20°C; 40 h; Hide Experimental Procedure

Rx-ID: 45192905 Find similar reactions

EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer

Patent: WO2017/64512 A1, 2017 ; Location in patent: Page/Page column 34; 55 ; Title/Abstract Full Text Show Details

General Procedure for the Syntheses of Compound 4

General procedure: Piperazine 3 (1 equiv.) and sodium cyanoborohydride (2 equiv.) were added successively as solids to a 0.1M solution of the R3 aldehyde (R3 as defined elsewhere) (1 equiv.) in methanol. The solution was allowed to stir at room temperature for 40 h. The solvent was removed under reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (x3). The organic extracts were combined and washed with brine, then dried (Na2SO4). The solvent was removed under reduced pressure. The crude product was purified by flash chromatography on deactivated silica gel, eluting with 2 - 5 percent methanol/ethyl acetate, to afford the product.

260

Synthesize Find similar

Rx-ID: 34159609 Find similar reactions

OTSUKA PHARMACEUTICAL CO., LTD.; KAWANO, Yoshikazu; HARAGUCHI, Yoshikazu; SASAKI, Hirofumi; UEMATSU, Yukitaka; TSUBOUCHI, Hidetsugu; YATA, Hiromi; SHIMIZU, Hiroshi; KOHASHI, Kazuho; ITOTANI, Motohiro; TAI, Kuninori; TAKEMURA, Isao; HAYASHI, Mikayo; HASHIZUME, Hiroyuki; MATSUBA, Miki; NAKAMURA, Izuru; CHEN, Xiuhao; MATSUMOTO, Makoto

Patent: WO2012/141338 A1, 2012 ; Location in patent: Page/Page column 330; 346 ; Title/Abstract Full Text Show Details


261

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Rx-ID: 16467 Find similar reactions

With nitrogen; toluene

Synthesize Find similar

Synthesize Find similar

Koo et al.

Journal of Organic Chemistry, 1959 , vol. 24, p. 179,183 Full Text View citing articles Show Details

262

Synthesize Find similar

Rx-ID: 39008196 Find similar reactions

47%

With copper(l) iodide; N-ethylN,N-diisopropylamine in acetonitrile

T=20°C; Hide Experimental Procedure

Synthesize Find similar

Synthesize Find similar

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 23 p. 5466 - 5469 Title/Abstract Full Text View citing articles Show Details

General procedure for the click reactions of 4-azido-2,8-bis(trifluoromethyl)quinoline with thecorresponding acetylenes

General procedure: 4-Azido-2,8-bis(trifluoromethyl)quinoline 8 (1.1 eq.) and the corresponding acetylene (1.0 eq.) were dissolved in CH3CN (1 mL). DIPEA (1.2 eq.) and CuI (0.25 eq.) were then added in that respective order. The solution was stirred overnight at rt and then concentrated. The mixture was diluted with DCM (20 mL) and washed with saturated NH4Cl solution (3 × 15 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification was done using the appropriate solvent system to offer the corresponding product as a solid.

263

Synthesize Find similar

Synthesize Find similar

Rx-ID: 39008219 Find similar reactions


Multi-step reaction with 4 steps 1: polyphosphoric acid / 3 h / 120 °C / |Inert atmosphere 2: trichlorophosphate / 5 h / 80 °C / |Inert atmosphere; |Reflux 3: sodium azide / N,N-dimethylformamide / 3 h / 55 °C / |Reflux; |Inert atmosphere 4: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C View Scheme

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 23 p. 5466 - 5469 Title/Abstract Full Text View citing articles Show Details

264

Synthesize Find similar

Multi-step reaction with 3 steps 1: trichlorophosphate / 5 h / 80 °C / |Inert atmosphere; |Reflux 2: sodium azide / N,N-dimethylformamide / 3 h / 55 °C / |Reflux; |Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C View Scheme

Synthesize Find similar

Rx-ID: 39008290 Find similar reactions

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 23 p. 5466 - 5469 Title/Abstract Full Text View citing articles Show Details

265

Synthesize Find similar

Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethylformamide / 3 h / 55 °C / |Reflux; |Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C View Scheme

Synthesize Find similar

Rx-ID: 39008302 Find similar reactions

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 23 p. 5466 - 5469 Title/Abstract Full Text View citing articles Show Details


266

Synthesize Find similar

Multi-step reaction with 2 steps 1: acetic acid / isopropyl alcohol; ethanol / 20 °C 2: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C View Scheme

Synthesize Find similar

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 23 p. 5466 - 5469 Title/Abstract Full Text View citing articles Show Details

267

Synthesize Find similar

Rx-ID: 23803970 Find similar reactions

JANSSEN PHARMACEUTICA N.V.

Patent: WO2006/67139 A1, 2006 ; Location in patent: Page/Page column 95 ;

Title/Abstract Full Text Show Details

268

Synthesize Find similar

Hide Experimental Procedure

Rx-ID: 39008314 Find similar reactions

Rx-ID: 24167113 Find similar reactions

SmithKline Beecham Corporation

Patent: US6552022 B1, 2003 ; Title/Abstract Full Text Show Details


A compound according to claim 1selected from the group consisting of: ... 4'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(4-(1-methyl-1H-pyrrol-2-ylmethyl)-piperazin-1-yl)-phenyl]-amide; 4'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(4-thiophen-2-ylmethyl-piperazin-1-yl)-phenyl]-amide; 4'-Trifluoromethyl-biphenyl-2-carboxylic acid {4-[4-(1H-pyrazole-3-ylmethyl)-piperazine-1-yl]-phenyl}-amide; 4'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(4-thiophen-3-ylmethyl-piperazin-1-yl)-phenyl]-amide; 4'-Trifluoromethyl-biphenyl-2-carboxylic acid {4-[4-(5-fluoro-1H-indol-3-ylmethyl)-piperazin-1-yl]-phenyl}-amide; 4'-Isopropyl-6-methoxy'-biphenyl-2-carboxylic acid (4-(4-(3-(3-methyl-[1,2,4]oxadiazol-5-yl)-benzyl)-piperazine-1-yl)-phenyl)-amide; 4'-Trifluoromethyl-biphenyl-2-carboxylic acid (4-{4-[3-(5-trifluoromethyl-1,2,4]oxadiazol-3-yl)-benzyl]-piperazin-1-yl}-phenyl)-amide;

269

Synthesize Find similar

Rx-ID: 23627746 Find similar reactions

OTSUKA PHARMACEUTICAL CO., LTD.

Patent: WO2005/105778 A2, 2005 ; Location in patent: Page/Page column 178 ;

Title/Abstract Full Text Show Details

270

Synthesize Find similar

Multi-step reaction with 3 steps 1.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane / 0.08 h / 0 °C / |Inert atmosphere 1.2: 1.5 h / 20 °C / |Inert atmosphere 2.1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C / |Inert atmosphere 3.1: dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere View Scheme

Synthesize Find similar

Rx-ID: 41493279 Find similar reactions

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.

Journal of Medicinal Chemistry, 2015 , vol. 58, # 23 p. 9179 - 9195 Title/Abstract Full Text View citing articles Show Details


271

Synthesize Find similar

Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C / |Inert atmosphere 2: dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere View Scheme

Synthesize Find similar

Rx-ID: 41493290 Find similar reactions

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.

Journal of Medicinal Chemistry, 2015 , vol. 58, # 23 p. 9179 - 9195 Title/Abstract Full Text View citing articles Show Details

272

Synthesize Find similar

Rx-ID: 41493298 Find similar reactions

90%

in dichloromethane

T=0 - 20°C; 2 h; Inert atmosphere;

Synthesize Find similar

Synthesize Find similar

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.

Journal of Medicinal Chemistry, 2015 , vol. 58, # 23 p. 9179 - 9195 Title/Abstract Full Text View citing articles Show Details

273

Synthesize Find similar

Rx-ID: 41493289 Find similar reactions

90%

in dichloromethane

T=0 - 20°C; 2 h; Inert atmosphere;

Synthesize Find similar

Synthesize Find similar

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.

Journal of Medicinal Chemistry, 2015 , vol. 58, # 23 p. 9179 - 9195 Title/Abstract Full Text View citing articles Show Details


274

Synthesize Find similar

Rx-ID: 41493359 Find similar reactions

Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C / |Inert atmosphere 2: dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere View Scheme

Synthesize Find similar

Synthesize Find similar

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.

Journal of Medicinal Chemistry, 2015 , vol. 58, # 23 p. 9179 - 9195 Title/Abstract Full Text View citing articles Show Details

275

Synthesize Find similar

Rx-ID: 41493302 Find similar reactions

91%

in dichloromethane

T=0 - 20°C; 2 h; Inert atmosphere;

Synthesize Find similar

Synthesize Find similar

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.

Journal of Medicinal Chemistry, 2015 , vol. 58, # 23 p. 9179 - 9195 Title/Abstract Full Text View citing articles Show Details

276

Synthesize Find similar

Rx-ID: 41493361 Find similar reactions

Multi-step reaction with 2

Synthesize Find similar

Synthesize Find similar

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.


steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C / |Inert atmosphere 2: dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere View Scheme

Journal of Medicinal Chemistry, 2015 , vol. 58, # 23 p. 9179 - 9195 Title/Abstract Full Text View citing articles Show Details


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