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

HRID 8922ノート

反応式

HRID 8922 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-84ad598adf5a425ab72a5d36c32f40d4
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

反応ノート

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