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

HRID 1582260ノート

反応式

HRID 1582260 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 222Ammonia溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-35ddbefa171941d0ab6ed1b7a107ff08
出典データセット
uspto-grants-2004_05
特許番号
US06734191B2

反応ノート

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