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Citations (37)
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1
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Rx-ID: 6518712 Find similar reactions
Tsuge,O. et al.
Tetrahedron, 1968 , vol. 24, p. 2583 - 2590 Full Text View citing articles Show Details
Biniecki; Moll
Acta Poloniae Pharmaceutica, 1974 , vol. 31, p. 731,732 Full Text Show Details
Macarovici; Boehm
Studia Universitatis Babes-Bolyai, Chemia, 1974 , vol. 19, p. 9,12 Chem.Abstr., vol. 82, # 73101m Full Text Show Details
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Shionogi BioResearch Corp.
Patent: US2003/45518 A1, 2003 ; Title/Abstract Full Text Show Details
6:The Following Compounds Shown Below Were Prepared by the Procedures Described Above.
The method was the same as one used in synthesis of 4783, oxalyl chloride was used instead of malonyl dichloride. 1H NMR (300 MHz, DMSO): δ 11.95 (s, 2H), 7.48-7.07(m, 10H), 3.52(s, 6H). ESMS cacld (C18H18N4O2S2):386.09; found: 387 (M+H)+.
1H
NMR (300 MHz, CDCl3): δ 9.66-8.83 (m, 2H), 3.73-3.23(m, 6H), 2.10-1.20 (m, 20H). ESMS cacld (C15H28N4O2S2):360.17; found: 359 (M-H)+.
1H 1H 1H 1H 1H 1H 1H 1H 1H 1H 1H 1H 1H
NMR (300 MHz, CDCl3): δ 3.66-3.42(m, 6H), 2.84-2.58(m, 4H), 1.40-1.19(m, 6H). ESMS cacld (C11H20N4O2S2):304.10; found: 303 (M-H)+. NMR (300 MHz, CDCl3): δ 4.15-3.40(m, 6H), 2.00-1.01(m, 14H). ESMS cacld (C14H22N4O2S2):342.12; found: 341 (M-H)+.
NMR (300 MHz, CDCl3): δ 3.90-3.18(m, 6H), 2.11-0.91 (m, 1 OH). ESMS cacld (C12H18N4O2S2):314.09; found: 313 (M-H)+.
NMR (300 MHz, CDCl3): δ 10.08-9.01(m, 2H), 3.68-3.20(m, 6H), 2.59-1.12(m, 16H). ESMS cacld (C15H24N4O2S2):356.13; found: 355 (M-H)+.
NMR (300 MHz, CDCl3): δ 10.22-9.41(m, 2H), 7.48-7.20(m, 5H), 3.82-3.02(m, 6H), 2.38-0.82(m, 7H). ESMS cacld (C16H20N4O2S2): 364.10; found: 363 (M-H)+. NMR (300 MHz, CDCl3): δ 10.03-9.02(m, 2H), 3.71-3.42(m, 6H), 2.80-0.81(m, 16H). ESMS cacld (C13H24N4O2S2): 332.13; found: 331 (M-H)+. NMR (300 MHz, CDCl3): δ 3.78-3.08(m, 6H), 1.90-0.81(m, 18H). ESMS cacld (C15H24N4O2S2): 356.13; found: 355 (M-H)+.
NMR (300 MHz, CDCl3): δ 10.00-8.79(m, 2H), 3.65-3.07(m, 6H), 2.79-1.08(m, 24H). ESMS cacld (C19H32N4O2S2): 412.20; found: 411 (M-H)+. NMR (300 MHz, CDCl3): δ 9.79(br, 2H), 3.79-3.41(m, 6H), 1.60-0.75(m, 18H). ESMS cacld (C15H24N4O2S2): 356.13; found: 355 (M-H)+.
NMR (300 MHz, CDCl3): δ 10.03-9.14(m, 2H), 4.21-3.39(m, 4H), 2.20-0.76(m, 18H). ESMS cacld (C15H24N4O2S2): 356.13; found: 355 (M-H)+.
NMR (300 MHz, CDCl3): δ 7.57(br, 2H), 3.72(s, 6H), 2.95(m, 6H), 1.96-0.81(m, 10H). ESMS cacld (C21H36N4O2S2):440.13; found: 439 (M-H)+. NMR (300 MHz, CDCl3): δ 10.09-8.95(m, 2H), 3.78-3.05(m, 6H), 2.04-1.22(m, 20H). ESMS cacld (C17H28N4O2S2):384.17; found: 383 (M-H)+.
NMR (300 MHz, CDCl3): δ 10.09-8.51(m, 2H), 7.41-7.01(m, 10H), 3.62-3.02(m, 6H), 1.78-1.03(m, 10H). ESMS cacld (C25H28N4O2S2): 480.17; found: 479 (M-H)+.
1H-NMR(300
MHz, CDCl3): ε 10.09-8.81(m, 2H), 7.51-7.11(m, 10H), 3.80-3.06(m, 6H), 2.92-1.53 (m, 110H). ESMS cacld (C25H28N4O2S2): 480.17; found: 479 (M-H)+.
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Broka, Chris Allen; Campbell, Jeffrey Allen
Patent: US2003/130337 A1, 2003 ; Title/Abstract Full Text Show Details
8:3-(2-Chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carbaldehyde
Example 8 3-(2-Chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carbaldehyde A solution of alcohol [3-(2-chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indol-2-yl]-methanol (75 mg) (prepared as described in Example 5) in CH2Cl2 (5 ml) was added to a solution of DMSO (0.2 ml) and oxalyl chloride (0.1 ml) that had been prepared at -78°.
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Emmanuel, Michel Jose; Hickey, Eugene R.; Liu, Weimin; Spero, Denice Mary; Sun, Sanxing; Thomson, David S.; Ward, Yancey David; Young, Erick Richard Roush
Patent: US2002/58809 A1, 2002 ; Title/Abstract Full Text Show Details
66.b:3-Cyano-3-{3-cyclohexyl-2-[(morpholine-4-carbonyl)-amino]-propionylamino}-pyrrolidine-1-carboxylic acid benzyl ester. (b) 3-Oxo-pyrrolidine-1-carboxylic acid benzyl ester. A solution of oxalyl chloride (12.6 g, 99 mmol, 2.0 equiv) was prepared in 250 mL of dry CH2Cl2 and cooled under Ar to -78° C. DMSO (15.5 g, 199 mmol, 4.0 equiv) was added dropwise over a 15 min period giving vigorous gas formation.
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Banyu Pharmaceutical Co Ltd
Patent: US6140333 A1, 2000 ; Title/Abstract Full Text Show Details
R.6.3:Step 3. Step 3. Synthesis of (2R,5R)-2-(t-butyl)-5-(3-oxocyclobutyl)-5-phenyl-1,3-dioxolan-4-one To a solution of 1.82 g of (2R,5R)-2-(t-butyl)-5-(3-benzyloxycyclobutyl)-5-phenyl-1,3-dioxolan-4-one, obtained by Step 2, in 40 ml of ethanol, 430 mg of palladium hydroxide-carbon catalyst was added, followed by stirring for 6 hours at ambient temperature under a hydrogen atmosphere. The reaction mixture was filtered with Celite, the solvent was distilled off under reduced pressure, and a solution of the resulting residue in 5 ml of dichloromethane was added dropwise at -78° C. to a reaction mixture resulting from the addition of 0.63 ml of oxalyl chloride to a solution of 1.1 ml of dimethylsulfoxide in 50 ml of dichloromethane at -78° C. and stirring for 5 minutes, followed by stirring for 15 minutes at the same temperature.
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BioChem Pharma Inc.
Patent: US5606037 A1, 1997 ; Title/Abstract Full Text Show Details
81:1-methoxy-3-(2-trimethyl ammonium ethyl amino carbonyl)-5,10-dioxo-5,10-dihydro-1H-naphtho-[2,3-c]-pyran chloride salt (BCH-2837) STR164 The acid I (20 mg, 0.07 mmol) in 2 ml of dichloromethane was treated with oxalyl chloride (9.2 μl, 0.105 mmol) and trace of DMF.
The crude liquid was evaporated and the solid residue was subjected to vacuum until oxalyl chloride was entirely pumped out. The acid chloride thus obtained was redissolved in THF. After chilled to -10° C., (2-aminoethyl)-trimethyl ammonium chloride hydrochloride (12.3 mg, 0.07 mmol) was added. This was followed by addition of diisopropyl ethyl amine (24.4 μl, 0.14 mmol). After 20 minutes, the solvent was evaporated. The crude product wetted with dichloromethane was filtered. The filtrate was concentrated to give a product which can be further purified on RP-8 silica gel. Yield 70percent. 1 H NMR (CDCl , 250 MHz, Bruker), δ: 1.39 (9H, br s, 3*CH ), 3.14 [2H, m, CH N(CH ) ], 3.62 (3H, s, OCH ), 3.74 (2H, m, NHCH ), 6.40 (1H, s, 1-H), 7.20 (1H, s, 4-H), 7.71 (2H, m, 7, 8-ArH), 8.10 (2H, m, 6, 9-ArH). IR (Nicolet, 205 FT, film on NaCl plate): cm-1, 3415.5, 2991.0, 2929.3, 2832.8, 2693.9, 2508.7, 1671.7, 1655.9, 1598.0, 1563.3, 1339.6, 1324.1, 1300.9, 1067.0, 3 3 2 3 3 3 2 989.6, 954.5, 864.4, 722.9.
Biochem Pharma Inc.
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Patent: US5736523 A1, 1998 ; Title/Abstract Full Text Show Details
46.9:1-methoxy-3-(2-pyridinyl) methyl amino[carbonyl]-3-methoxy-5,10-dioxo-5,10-dihydro-1H-naphtho-[2,3-c]-pyran(BCH-2840)
Step 9 1-methoxy-3-(2-pyridinyl) methyl amino[carbonyl]-3-methoxy-5,10-dioxo-5,10-dihydro-1H-naphtho-[2,3-c]-pyran(BCH-2840) Preparative details: See example 16, step 7. compound I: 20 mg, 0.07 mmol Oxalyl chloride: 9.2 μl, 0.10 mmol compound II: 23 mg 1 H NMR (CDCl , 250 MHz, Bruker), δ: 3.65 (3H, s, OCH ), 4.72 (2H, d, J=5.4 Hz, NHCH ), 6.43 (1H, s, 1-H), 7.23 (1H, m, py-H), 7.30 (1H, d, J=7.9 Hz, py-H), 7.38 (1H, s, 4-H), 7.69 (1H, tr d, J=8.9 Hz, 1.2 Hz, py-H), 7.75 (2H, m, 7, 8-ArH), 8.12 (2H, m, 6, 9-ArH), 8.12 (1H, overlapped, NHCO), 8.56 (1H, d, J=4.2 Hz, py-H). 3 3 2 IR (Nicolet, 205 FT, film on NaCl plate): cm-1, 3360.1, 2934.7, 1675.5, 1655.5, 1595.5, 1518.4, 1292.9, 1270.0, 1084.4, 950.23, 861.04, 719.77.
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Bayer Aktiengesellschaft
Patent: US4341720 A1, 1982 ; Title/Abstract Full Text Show Details
1:EXAMPLE 1
EXAMPLE 1 1,000 g of phosphorus pentachloride and 12 g of triethylamine are suspended in 500 g of phosphorus oxychloride in a 2 l four-necked flask with a stirrer, solids metering funnel and distillation attachment. 100 g of anhydrous oxalic acid are introduced at a reaction temperature of 60° C. and under an operating pressure of 250 mbars in the course of 40 minutes. Finally, the mixture is subsequently stirred at 70° C. and under 250 mbars for 30 minutes. During the metering time and subsequent stirring time, 497 g of a mixture containing 20.7percent by weight of oxalyl chloride and 78.4percent by weight of phosphorus oxychloride are obtained in the distillation receiver.
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Bayer Aktiengesellschaft
Patent: US4341720 A1, 1982 ; Title/Abstract Full Text Show Details
21:EXAMPLE 21
EXAMPLE 21 1,500 g of phosphorus oxychloride, 100 g of 2,4-dimethylpyridine and 1,980 g of phosphorus trichloride are initially introduced in an apparatus according to Example 19. 1,040 g of chlorine are then passed in over a period of about 2 hours, the mixture being allowed to boil under reflux at a bottom temperature of about 124° C. The excess chlorine is distilled off, the mixture is cooled to 60° C. and 420 g of anhydrous oxalic acid are introduced at a reaction temperature of 60° C. and under an operating pressure of 240 mbars in the course of 4 hours, whilst stirring. 1,813 g of crude distillate containing 26.8percent by weight of oxalyl chloride are isolated, from which 481 g of oxalyl chloride can be obtained by rectification.
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Ciba-Geigy Corporation
Patent: US4007156 A1, 1977 ; Title/Abstract Full Text Show Details
By following the above procedure, and substituting for the stearoyl chloride an equivalent amount of: a. oxalyl dichloride b. benzoyl chloride c. phthaloyl chloride d. isophthaloyl chloride e. terephthaloyl chloride
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SmithKline Corporation
Patent: US4242346 A1, 1980 ; Title/Abstract Full Text Show Details
Following the procedure of Example 9 and substituting the following for adipoyl chloride: Oxalyl chloride Malonyl chloride Succinyl chloride Glutaryl chloride
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Lerchen, Hans-Georg; Siegmund, Hans-Ulrich; Immler, Dorian; Schumacher, Andreas; Auriel, Daniel
Patent: US2005/49406 A1, 2005 ; Title/Abstract Full Text Show Details
Intermediate Series 3: Oligopiperazine Derivatives
The preparation was effected in analogy with the Example I.3.7 using the building blocks: Fmoc-piperidine
Oxalyl chloride Compound from Example SC.2.7 Compound from Example SC.2.9. Yield: 38percent over 4 steps [TLC: Rf=0.4 7)] [ESI-MS: m/e=586 (M+H)+].
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Lerchen, Hans-Georg; Siegmund, Hans-Ulrich; Immler, Dorian; Schumacher, Andreas; Auriel, Daniel
Patent: US2005/49406 A1, 2005 ; Title/Abstract Full Text Show Details
Intermediate Series 3: Oligopiperazine Derivatives
The preparation was effected in analogy with Example I.3.7 using the building blocks: Compound from Example SC.2.8 Oxalyl chloride Compound from Example SC.2.7 Compound from Example SC.2.9. Yield: 41percent over 4 steps [TLC: Rf=0.55 4)].
[ESI-MS: m/e=592 (M+H)+].
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MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
1:Step 1
Step 1 Following general procedure A using bicyclo[1.1.1]pentane-1,3-dicarboxylic acid 89 (31 mg, 0.20 mmol), oxalyl chloride (0.025 mL, 0.40 mmol), THF (8 mL) and 1 drop of DMF, 90 was prepared as an off white solid (40 mg, quant.). Crude 90 was used immediately in the next step as is.
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MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
1:Step 1
Step 1 Following general procedure A using bicyclo[2.1.1]hexane-1,4-dicarboxylic acid 80 (30 mg, 0.18 mmol), oxalyl chloride (0.0303 mL, 0.353 mmol), THF (4 mL) and 1 drop of DMF, 81 was prepared as an off white solid (39 mg, quant.). Crude 81 was used immediately in the next step as is.
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MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
1:Step 1
Step 1 Following general procedure A using bicyclo[2.2.1]heptane-1,4-dicarboxylic acid 86 (16 mg, 0.087 mmol), oxalyl chloride (0.016 mL, 0.18 mmol), THF (5 mL) and 1 drop of DMF, 87 was prepared as an off white solid (19 mg, 99percent). Crude 87 was used immediately in the next step as is.
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MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
1:Step 1
Step 1 Following general procedure A using bicyclo[2.2.2]octane-1,4-dicarboxylic acid 83 (16 mg, 0.081 mmol), oxalyl chloride (0.015 mL, 0.17 mmol), THF (5 mL) and 1 drop of DMF, 84 was prepared as an off white solid (19 mg, quant.). Crude 84 was used immediately in the next step as is.
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MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
2:Step 2
Step 2 Following general procedure A using 76 (90 mg, 0.40 mmol), oxalyl chloride (0.033 mL, 0.39 mmol), THF (8 mL) and 1 drop of DMF, 77 was prepared as an off white solid (79 mg, quant.). Crude 77 was used immediately in the next step as is. A
B
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2
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Rx-ID: 40427473 Find similar reactions
MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
1:Step 1
Step 1 Following general procedure A using 3-(tert-butoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid 105 (212 mg, 1.0 mmol), oxalyl chloride (0.094 mL, 1.10 mmol), THF (3 mL), dichloromethane (6 m) and 1 drop of DMF, 105 was prepared as an off white solid (235 mg, quant.). Crude 105 was used immediately in the next step as is.
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MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
4:Step 4
Step 4 Following general procedure A using 95 (55 mg, 0.101 mmol), oxalyl chloride (0.0104 mL, 0.121 mmol), THF (3 mL), dichloromethane (1 mL) and 1 drop of DMF, 96 was prepared as an off white solid (46 mg, quant.). Crude 96 was used immediately in the next step as is.
3
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Rx-ID: 40427488 Find similar reactions
MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
1:Step 1
Step 1 Following general procedure A using 3-(2-tert-butoxy-2-oxoethyl)bicyclo[1.1.1]pentane-1-carboxylic acid 92 [prepared as described in Bioorg. Med. Chem. 2009, 17, 242-250.] (90 mg, 0.40 mmol), oxalyl chloride (0.041 mL, 0.477 mmol), THF (8 mL) and 1 drop of DMF, 93 was prepared as an off white solid (103 mg, quant.).
Crude 93 was used immediately in the next step as is.
4
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Rx-ID: 40427491 Find similar reactions
MADERNA, Andreas; DOROSKI, Matthew David; CHEN, Zecheng; RISLEY, Hud Lawrence; CASAVANT, Jeffrey Michael; O'DONNELL, Christopher John; PORTE, Alexander M.; SUBRAMANYAM, Chakrapani
Patent: US2015/209445 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
2:Step 2
Step 2 Following general procedure B using 11 (311 mg, 0.997 mmol), 105 (230 mg, 0.997 mmol), triethylamine (0.292 mL, 2.09 mmol) and THF (20 mL), and purification using silica gel chromatography (Gradient: 10percent to 75percent acetone in heptane). Appropriate test tubes where combined and concentrated in vacuo producing a white solid. To a stirring solution of crude material in 10 mL of dichloromethane, TFA (5.0 mL, 65 mmol) was added. The reaction was allowed to stir at room temperature for ˜90 minutes. Reaction was concentrated in vacuo. Material was dissolved with dichloromethane, transferred to a separatory funnel and then washed with 1N HCl aq., brine, and water. Organic layer was dried over sodium sulfate, filtered, and then concentrated in vacuo before being placed underneath high vacuum producing a white solid. Using this crude material and following general procedure A with oxalyl chloride (0.010 mL, 0.121 mmol), THF (4 mL), dichloromethane (2 mL) and 1 drop of DMF, 107 was prepared as a white solid (52 mg, 49percent, 3 steps). Crude 107 was used immediately in the next step as is.
5
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Rx-ID: 33187999 Find similar reactions
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With triethylamine in dichloromethane; water
Chung-Ang University Industry-Academiy Cooperation Foundation
Patent: US2012/135532 A1, 2012 ;
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Title/Abstract Full Text Show Details
1:Preparation of Resorufin Compounds
Mass spectrums were obtained from Micromass Autospec Mass Spectrometer. To prepare resorufin compounds, oxalyl chloride (0.82 mL, 8.6 mmol) and DMF (15 μl) were added to a suspension of levulinic acid (500 mg, 4.3 mmol) dissolved in dichloromethane (50 mL). The reaction mixture was stirred at room temperature for 4 hours, and then volatile materials were distilled under reduced pressure and the residue was dried via vacuum pumping. The residue was dissolved in a small amount of dry dichloromethane. The above solution was slowly added to the dispersed dichloromethane solution (50 mL) containing resorufin sodium salt (300 mg, 1.3 mmol) and triethylamine (0.54 mL, 3.9 mmol). After stirring the mixture for 12 hours, the reaction mixture was filtered off and the resulting solution was treated with water. The organic phase was separated, washed with 1M sodium bicarbonate solution and water, and then distilled to obtain a residue in a solid phase. The final product was crystallized from ethyl acetate and purified. The yield was 75percent. 1H NMR (600 MHz, CDCl ) d7.77 (d, J=8.6 Hz, 1H), 7.41 (d, J=9.8 Hz, 1H), 7.13 (s, 1H), 7.12 (d, J=8.6 Hz, 1H), 6.84 (d, J=9.8 Hz, 1H), 6.30 (s, 1H), 2.89 (m, 2H), 2.83 (m, 2H), 2.23 (s, 3H); 3 13C
NMR (150 MHz, CDCl3) d206.1, 186.3, 170.7, 153.5, 149.3, 148.2, 144.3, 135.1, 134.8, 131.2, 131.1, 119.3, 109.7, 107.2, 37.8, 29.8, 28.2;
HRMS (DPI); m/z calcd for C17H13NO5 [M]+: 311.0794, found 311.0786.
6
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With phosphorus pentachloride
T=20°C; 72 h;
Rx-ID: 11037677 Find similar reactions
George, Lisa; Netsch, Klaus-Peter; Penn, Gerhard; Kollenz, Gert; Wentrup, Curt
Organic and Biomolecular Chemistry, 2006 , vol. 4, # 3 p. 558 - 564 Title/Abstract Full Text View citing articles Show Details
A
B
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7
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Rx-ID: 25858160 Find similar reactions
Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.
Patent: US2005/26944 A1, 2005 ; Title/Abstract Full Text Show Details
2:N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-(3-chlorophenyl)urea
EXAMPLE 2 N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-(3-chlorophenyl)urea The desired product was prepared by substituting 1-isocyanato-3-chlorobenzene for 1-isocyanato-3-methylbenzene in Example 1. 1H NMR (300 MHz, DMSO-d6) δ 5.44 (s, 2H), 7.06 (ddd, J=7.8, 2.0, 1.4 Hz, 1H), 7.24-7.25 (m, J=1.7 Hz, 1H), 7.27 (d, J=5.4 Hz, 1H), 7.26-7.27 (m, 1H), 7.34 (t, J=8.1 Hz, 1H), 7.39 (dd, J=11.9, 2.0 Hz, 1H), 7.50 (s, 1H), 7.75 (t, J=2.0 Hz, 1H), 7.84 (d,
J=5.8 Hz, 1H), 8.27 (t, J=8.5 Hz, 1H), 8.78 (d, J=2.4 Hz, 1H), 9.32 (s, 1H); MS (ESI(+)) m/e 413.0, 415.1 (M+H)+. A
B
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8
Rx-ID: 25858161 Find similar reactions
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Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.
Patent: US2005/26944 A1, 2005 ; Title/Abstract Full Text Show Details
4:N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-[2-fluoro-5-(trifluoromethyl)phenyl]urea
EXAMPLE 4 N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-[2-fluoro-5-(trifluoromethyl)phenyl]urea The desired product was prepared by substituting 1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene for 1-isocyanato-3-methylbenzene in Example 1. 1H NMR (300 MHz, DMSO-d6) δ 5.43 (s, 2H), 7.26 (dd, J=9.0, 2.2 Hz, 1H), 7.28 (d, J=5.4 Hz, 1H), 7.41 (dd, J=12.0, 1.9 Hz, 1H), 7.40-7.45 (m, 1H), 7.51 (s, 1H), 7.53 (dd, J=11.2, 8.5 Hz, 1H), 7.85 (d, J=5.8 Hz, 1H), 8.32 (t, J=8.5 Hz,
1H), 8.66 (dd, J=7.3, 2.2 Hz, 1H), 9.33 (d, J=2.4 Hz, 1H), 9.45 (d, J=2.7 Hz, 1H); MS (ESI(+)) m/e 465.0 (M+H)+. A
B
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9
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Rx-ID: 25858162 Find similar reactions
Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.
Patent: US2005/26944 A1, 2005 ; Title/Abstract Full Text Show Details
5:N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-(3-bromophenyl)urea
EXAMPLE 5 N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-(3-bromophenyl)urea The desired product was prepared by substituting 1-bromo-3-isocyanatobenzene for 1-isocyanato-3-methylbenzene in Example 1. 1H NMR (300 MHz, DMSO-d6) δ 5.44 (s, 2H), 7.19 (dt, J=7.1, 1.9 Hz, 1H), 7.24-7.33 (m, 4H), 7.39 (dd, J=11.9, 2.0 Hz, 1H), 7.50 (s, 1H), 7.84 (d, J=5.8 Hz, 1H), 7.89-7.91 (m, 1H), 8.27 (t, J=8.5 Hz, 1H), 8.77 (d, J=2.7 Hz, 1H), 9.31 (s, 1H); MS (ESI(+))
m/e 457.0, 458.8 (M+H)+.
A
B
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10
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Rx-ID: 25858163 Find similar reactions
Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.
Patent: US2005/26944 A1, 2005 ; Title/Abstract Full Text Show Details
3:N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-[3-(trifluoromethyl)phenyl]urea
EXAMPLE 3 N-[4-(4-aminothieno[3,2-c]pyridin-3-yl)-2-fluorophenyl]-N'-[3-(trifluoromethyl)phenyl]urea The desired product was prepared by substituting 1-isocyanato-3-trifluoromethylbenzene for 1-isocyanato-3-methylbenzene in Example 1. 1H NMR (300 MHz, DMSO-d6) δ 5.45 (s, 2H), 7.26 (dd, J=8.1, 1.7 Hz, 1H), 7.28 (d, J=5.8 Hz, 1H), 7.34-7.37 (m, 1H), 7.40 (dd, J=12.0, 1.9 Hz, 1H), 7.51 (s, 1H), 7.54-7.57 (m, 2H), 7.84 (d, J=5.4 Hz, 1H), 8.06 (s, 1H), 8.27 (t, J=8.5 Hz, 1H),
8.81 (d, J=2.4 Hz, 1H), 9.47 (s, 1H); MS (ESI(+)) m/e 447.0 (M+H)+.
11
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Rx-ID: 553730 Find similar reactions
With phosphorus pentachloride; trichlorophosphate
Smith; Holmes
Journal of the American Chemical Society, 1951 , vol. 73, p. 4294,4297 Full Text View citing articles Show Details
With phosphorus pentachloride
Biltz; Topp
Chemische Berichte, 1913 , vol. 46, p. 1399 Full Text Show Details
Staudinger; Anthes
Chemische Berichte, 1913 , vol. 46, p. 1435 Full Text Show Details
Staudinger
Patent: DE216919 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 81 Full Text Show Details
Staudinger
Patent: DE216918 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 80 Full Text Show Details
With phosphorus pentachloride
Staudinger
Chemische Berichte, 1908 , vol. 41, p. 3566 Full Text Show Details
With phosphorus pentachloride
Heating;
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.
Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 7 p. 1737 - 1749 Title/Abstract Full Text View citing articles Show Details
12
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Patent: US6362336 B1, 2002 ; Location in patent: Example 56 ;
in formamide
T=150°C; 6 h;
Title/Abstract Full Text Show Details
A
B
Rx-ID: 22879265 Find similar reactions
13
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Rx-ID: 24005866 Find similar reactions
Emmanuel, Michel Jose; Hickey, Eugene R.; Liu, Weimin; Spero, Denice Mary; Sun, Sanxing; Thomson, David S.; Ward, Yancey David; Young, Erick Richard Roush
Patent: US2002/58809 A1, 2002 ; Title/Abstract Full Text Show Details
62.b:Morpholine-4-carboxylic acid [1-(3-cyano-1-cyclopropylmethyl-pyrrolidin-3-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide. (b) 1-Cyclopropylmethyl-pyrrolidin-3-one. A solution of oxalyl chloride (13.1 g, 103 mmol, 2.0 equiv) was prepared in 200 mL of dry CH2Cl2 and cooled under Ar to -78° C. DMSO (16.1 g, 206 mmol, 4.0 equiv) was added as a solution in 20 mL of CH2Cl2 dropwise over a 30 min period giving vigorous gas formation. A
B
C
D
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14
Synthesize Find similar Rx-ID: 8553408 Find similar reactions
With BaY-coated optical fibers; oxygen
Solid phase reaction; Oxidation; Irradiation; Product distribution;
Pradhan, Ajit R.; Macnaughtan, Megan A.; Raftery, Daniel
Journal of the American Chemical Society, 2000 , vol. 122, # 2 p. 404 - 405 Title/Abstract Full Text View citing articles Show Details
15
Synthesize Find similar With pyridine; osmium(VIII) oxide
1) n-hexane, r.t., 2) 150 deg C; Yield given. Multistep reaction;
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Rx-ID: 1764140 Find similar reactions
Herrmann, Wolfgang A.; Eder, Stefan J.
Chemische Berichte, 1993 , vol. 126, # 1 p. 31 - 38 Title/Abstract Full Text Show Details
A
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C
D
E
F
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16
Synthesize Find similar Rx-ID: 8426397 Find similar reactions
With oxygen
Krespan, Carl G.; Dixon, David A.
Journal of Organic Chemistry, 1991 , vol. 56, # 12 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details
A
B
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17
Synthesize Find similar Rx-ID: 8427677 Find similar reactions
B: 32%
With oxygen
T=28 - 40°C; P=500 - 600 Torr;
Krespan, Carl G.; Dixon, David A.
Journal of Organic Chemistry, 1991 , vol. 56, # 12 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details
B: 32%
With oxygen
T=28 - 40°C; P=500 - 600 Torr;
Krespan, Carl G.; Dixon, David A.
Journal of Organic Chemistry, 1991 , vol. 56, # 12 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details
18
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Rx-ID: 1984312 Find similar reactions
With phosphorus pentachloride
T=20°C; 168 h; Yield given;
Kollenz, Gert; Penn, Gerhard; Dolenz, Gerhard; Akcamur,Yunus; Peters, Karl; et al.
Chemische Berichte, 1984 , vol. 117, # 4 p. 1299 - 1309 Title/Abstract Full Text Show Details
A
B
C
D
E
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19
Synthesize Find similar Rx-ID: 3402236 Find similar reactions
E: 83.7%
With phosphorus pentachloride; manganese (II) chloride
T=90°C; 5 h; other catalysts (CuCl2, ZnCl2, CdCl2, CrCl3, FeCl3, CoCl2, PdCl2) and temperatures (from 70 to 130 deg C); Product distribution;
Chernyuk, G. P.; Poludnenko, V. G.; Bel'ferman, A. L.
J. Appl. Chem. USSR (Engl. Transl.), 1982 , vol. 55, # 9 p. 2058 - 2061,1893 - 1895 Title/Abstract Full Text Show Details
20
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Rx-ID: 7386318 Find similar reactions
Cameron et al.
Arzneimittel Forschung, 1973 , vol. 23, p. 708,709 Full Text Show Details
A
B
C
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21
Synthesize Find similar Rx-ID: 234744
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Baganz et al.
Chemische Berichte, 1958 , vol. 91, p. 1751,1757 Full Text Show Details
T=165°C;
A
B
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22
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Rx-ID: 21753 Find similar reactions
Du Pont de Nemours and Co.
Patent: US2816141 , 1955 ; Full Text Show Details
23
Synthesize Find similar With pyridine; chlorobenzene
Synthesize Find similar Du Pont de Nemours and Co.
Patent: US2816141 , 1955 ; Full Text Show Details
24
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Rx-ID: 6518713 Find similar reactions
Rx-ID: 254913 Find similar reactions
With pumice stone; chlorine
T=200°C; P=147102 Torr;
Standard Oil Devel.Co.
Patent: US2055617 , 1931 ;
With metal halide; chlorine
T=200°C; P=147102 Torr;
Standard Oil Devel.Co.
Patent: US2055617 , 1931 ;
With chlorine; carbon
T=200°C; P=147102 Torr;
Standard Oil Devel.Co.
Patent: US2055617 , 1931 ;
Full Text Show Details
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25
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With carbon
T=200°C; P=147102 Torr;
Standard Oil Devel.Co.
Patent: US2055617 , 1931 ;
With pumice stone
T=200°C; P=147102 Torr;
Standard Oil Devel.Co.
Patent: US2055617 , 1931 ;
With metal halide
T=200°C; P=147102 Torr;
Standard Oil Devel.Co.
Patent: US2055617 , 1931 ;
Rx-ID: 6518714 Find similar reactions
Full Text Show Details
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26
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Rx-ID: 5436041 Find similar reactions
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Staudinger
Chemische Berichte, 1908 , vol. 41, p. 3566 Full Text Show Details
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Staudinger; Anthes
Chemische Berichte, 1913 , vol. 46, p. 1435 Full Text Show Details
Staudinger
Patent: DE216919 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 81 Full Text Show Details
Staudinger
Patent: DE216918 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 80 Full Text Show Details
27
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beim Erhitzen;
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Rx-ID: 726714 Find similar reactions
Fauconnier
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1892 , vol. 114, p. 122 Ber., vol. 25, p. Ref., 110 Full Text Show Details
Jones; Tasker
Journal of the Chemical Society, 1909 , vol. 95, p. 1905 Chem. Zentralbl., 1909 , vol. 80, # II p. 590 Full Text Show Details
Staudinger
Chemische Berichte, 1908 , vol. 41, p. 3558,3562 Full Text Show Details
28
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Rx-ID: 5802266 Find similar reactions
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Fauconnier
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1892 , vol. 114, p. 122 Ber., vol. 25, p. Ref., 110 Full Text Show Details
Staudinger
Chemische Berichte, 1908 , vol. 41, p. 3566 Full Text Show Details