Methanol → 5-Aminomethyl-2-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzoic acid methyl ester

HRID 8922노트

반응식

HRID 8922 반응식
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][N:18]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=1[C:38]([O:40][CH3:41])=[O:39])[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.CO>N.[Ni]>[CH3:41][O:40][C:38](=[O:39])[C:31]1[CH:32]=[C:33]([CH2:36][NH2:37])[CH:34]=[CH:35][C:30]=1[CH2:29][N:18]([CH2:17][C:9]1[NH:8][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1

참가 물질

5

반응물 2

HCID 887MethanolHCID 686195052-{[(4-Cyano-2-methoxycarbonyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 207256295-Aminomethyl-2-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzoic acid methyl ester수율 71%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 222Ammonia용매

실험 절차

A solution of 2-{[(4-cyano-2-methoxycarbonyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester (710 mg, 1.29 mmol) in saturated NH3(g)/MeOH (25 mL) was shaken at room temperature with a suspension of Raney® nickel (1.2 g) under hydrogen atmosphere (50 psi) for 17 h. The catalyst was removed by filtration over celite, and the filtrate was concentrated in vacuo. The crude material was filtered through silica gel (20:1:1 CH2Cl2/MeOH/NH4OH) to give a white foam (416 mg, 71%).

후처리

  1. customThe catalyst was removed by filtration over celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. filtrationThe crude material was filtered through silica gel (20:1:1 CH2Cl2/MeOH/NH4OH)

출처 및 근거

ORD 기록
ord-84ad598adf5a425ab72a5d36c32f40d4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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