Sodium hydride → 6-chloro-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)pyridine-3-carboxamide

HRID 2190518

반응식

HRID 2190518 반응식
[CH3:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Na+].[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][N:18]=1.C(N(C(C)C)CC)(C)C>O1CCCC1.C(Cl)Cl.CO>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:7][C:5]2[S:6][C:2]([CH3:1])=[C:3]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:4]=2)=[O:22])=[CH:19][N:18]=1

참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 961292-Amino-4-phenyl-5-methylthiazoleHCID 27821656-Chloronicotinoyl Chloride

생성물 1

HCID 33799416-chloro-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)pyridine-3-carboxamide수율 29%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a mixture of 5-methyl-4-phenyl-thiazol-2-ylamine (2.0 g, 10.5 mmol) in anhydrous tetrahydrofuran (40 mL) and methylene chloride (40 mL) in a round bottom flask under argon was carefully added sodium hydride (60% in mineral oil, 1.7 g, 42.5 mmol). The mixture was heated in a 60° C. oil bath for one hour, then chilled in an ice bath and 6-chloro-nicotinoyl chloride (2.03 g, 11.6 mmol) was added followed by diisopropylethylamine (7.32 mL, 42.1 mmol). The mixture was heated under argon in an oil bath at 60° C. for two hours and stirred at room temperature overnight. After dilution with methanol, the mixture was loaded onto silica gel and chromatographed using a mixture of ethyl acetate/hexanes to give 6-chloro-N-(5-methyl-4-phenyl-thiazol-2-yl)-nicotinamide (1.0 g, Yield: 29%).

후처리

  1. temperaturechilled in an ice bath
  2. temperatureThe mixture was heated under argon in an oil bath at 60° C. for two hours
  3. customchromatographed
  4. additiona mixture of ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-9c86738ae61c4b5dbae48a38b4074f07
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324385B2

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