7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-methylthio-2,3,6,7-tetrahydro-1,4-thiazepine → 3-[1-(4-Bromo-3-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

HRID 1424026노트

반응식

HRID 1424026 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([NH:13][NH2:14])=O)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:15].[Si:16]([O:23][CH2:24][C:25]1([CH3:34])[S:31][CH2:30][CH2:29][N:28]=[C:27](SC)[CH2:26]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(O)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[N:28]4[CH2:29][CH2:30][S:31][C:25]([CH2:24][O:23][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])([CH3:34])[CH2:26][C:27]4=[N:14][N:13]=3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:15]

참가 물질

4

반응물 2

HCID 685222157-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-methylthio-2,3,6,7-tetrahydro-1,4-thiazepineHCID 867128771-(4-Bromo-3-fluorophenyl)cyclopropanecarbohydrazide

생성물 1

HCID 867128783-[1-(4-Bromo-3-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine수율 44%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A solution of the compound (4.1 g, 15 mmol) obtained in Example 25-2) and 7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepine (4.79 g, 15 mmol) in n-butanol (30 mL) was stirred at 140° C. for 3.5 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Isco Combiflash, 40 g, ethyl acetate:dichloromethane=0:100 to 100:0, gradient) to obtain the title compound (3.47 g, 44%) as a brown solid.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (Isco Combiflash, 40 g, ethyl acetate:dichloromethane=0:100 to 100:0, gradient)

출처 및 근거

ORD 기록
ord-819333a8a68d4fa28cf94d8cffdb8049
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927536B2

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