Pyridine → 4-{2-Cyclohexyl-2-[5,6-difluoro-2-((S)-methoxy-phenyl-methyl)-benzoimidazol-1-yl]-acetylamino}-benzoic acid ethyl ester

HRID 1099467노트

반응식

HRID 1099467 반응식
[CH:1]1([CH:7]([N:11]2[C:15]3[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=3[N:13]=[C:12]2[C@@H:22]([O:29][CH3:30])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8](O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.S(Cl)(Cl)=O.[NH2:41][C:42]1[CH:52]=[CH:51][C:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:44][CH:43]=1>ClCCl>[CH2:49]([O:48][C:46](=[O:47])[C:45]1[CH:51]=[CH:52][C:42]([NH:41][C:8](=[O:9])[CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:11]2[C:15]3[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=3[N:13]=[C:12]2[C@@H:22]([O:29][CH3:30])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:43][CH:44]=1)[CH3:50]

참가 물질

6

반응물 4

HCID 1049Pyridine2회HCID 2337BenzocaineHCID 24386Thionyl ChlorideHCID 66810386Cyclohexyl-[5,6-difluoro-2-((S)-methoxy-phenyl-methyl)-benzoimidazol-1-yl]-acetic acid

생성물 1

HCID 668104074-{2-Cyclohexyl-2-[5,6-difluoro-2-((S)-methoxy-phenyl-methyl)-benzoimidazol-1-yl]-acetylamino}-benzoic acid ethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of cyclohexyl-[5,6-difluoro-2-((S)-methoxy-phenyl-methyl)-benzoimidazol-1-yl]-acetic acid (160 mg, 0.39 mmol, 1.0 equiv.) in dichloromethane (2 ml) was added pyridine (0.046 ml, 1.5 equiv.). Thionyl chloride (0.034 ml, 1.2 eq) was added dropwise. The mixture was stirred 1 h at room temperature. A solution of ethyl 4-amino-benzoate (64 mg, 0.95 equiv., [CAS RN 94-09-7]) and pyridine (0.031 ml, 1.1 equiv.) in dichloromethane (2 ml) was added and the mixture stirred overnight at room temperature. The mixture was applied to a 5 g silica gel column (Biotage) and the product eluted with EtOAc to afford the title compound as an orange solid that was used without further purification. MS (ISP): 562.3 [M+H]+.

후처리

  1. stirringthe mixture stirred overnight at room temperature
  2. washthe product eluted with EtOAc

출처 및 근거

ORD 기록
ord-f8ebb8828faa45a0b8fdc82b9ad52616
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143422B2

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