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

HRID 8922Notes

Reaction equation

HRID 8922 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-84ad598adf5a425ab72a5d36c32f40d4
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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