Dimethylformamide → HCID 57937599, 화합물

HRID 1435136노트

반응식

HRID 1435136 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11]1[CH:12]=[C:13]([N:20]2[C:24]3[CH:25]=[CH:26][C:27]([C:29](O)=[O:30])=[CH:28][C:23]=3[N:22]=[CH:21]2)[S:14][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH3:9].C(N(C(C)C)CC)(C)C.[C:41]([NH:44][NH2:45])(=[O:43])[CH3:42].CN(C=O)C>C(Cl)Cl.O>[C:41]([NH:44][NH:45][C:29]([C:27]1[CH:26]=[CH:25][C:24]2[N:20]([C:13]3[S:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([O:10][C@@H:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH3:9])[CH:12]=3)[CH:21]=[N:22][C:23]=2[CH:28]=1)=[O:30])(=[O:43])[CH3:42]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 685699691-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid2회

생성물 1

HCID 57937599HCID 57937599, 화합물수율 91.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A 20.0 mL flask was charged with 150 mg (0.329 mmol) of 1-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid (Intermediate 34, 0.120 mL, 0.658 mmol) of diisopropyl ethylamine, 24.4 mg (0.329 mmol) of acethydrazide and 2.00 ml of DMF. Next, 125 mg (0.329 mmol) of O-(7-Aza benzotriazole-1-yl)-N,N,N′,N′ tetramethyluranium hexafluoro phosphate was added and the reaction mixture stirred at rt for 30 min. 10 mL of water and 30 mL of DCM was added and the organic layer separated. The organic layer was adsorbed onto silica gel and chromatographed to give 154 mg (91% yield) of a tan solid. MS (APCI): 513 [M+H]+.

후처리

  1. customthe organic layer separated
  2. customchromatographed

출처 및 근거

ORD 기록
ord-252524b17ac3428a9a2e177da461c5a4
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615643B2

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