[3-(3-benzyl-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-cyclohexyl]-carbamic acid benzyl ester → 2-(3-Amino-cyclohexyl)-3-benzyl-5-methyl-3,5-dihydro-imidazo[4,5-c]quinolin-4-one

HRID 1376235Notes

Reaction equation

HRID 1376235 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[N:31]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:20]3[C:21](=[O:30])[N:22]([CH3:29])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:19]=3[N:18]=2)[CH2:12]1)C1C=CC=CC=1>[Pd]>[NH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[N:31]([CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:20]3[C:21](=[O:30])[N:22]([CH3:29])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:19]=3[N:18]=2)[CH2:12]1

Participants

3

Reactant 1

HCID 58788443[3-(3-benzyl-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-cyclohexyl]-carbamic acid benzyl ester

Product 1

HCID 160456872-(3-Amino-cyclohexyl)-3-benzyl-5-methyl-3,5-dihydro-imidazo[4,5-c]quinolin-4-oneYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

As described in example 3F, [3-(3-benzyl-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-cyclohexyl]-carbamic acid benzyl ester (70 mg, 0.135 mmol) was hydrogenated over 10% Pd/C (70 mg, 0.066 mmol) to give 2-(3-amino-cyclohexyl)-3-benzyl-5-methyl-3,5-dihydro-imidazo[4,5-c]quinolin-4-one (45 mg, 87% yield). The HCl salt was prepared by treating the amine in EtOAc with ethereal HCl (0.3 mL). 1H-NMR (CD3OD): δ 8.53 (d, 1H,J=8.0 Hz), 7.78 (m, 2H), 7.53 (m, 1H), 7.36 (m, 5H), 6.38 (m, 1H), 6.13 (m, 1H), 3.84 (s, 3H), 3.53 (m, 1H), 3.34 (m, 1H), 2.17 (m, 2H), 1.94 (m, 2H), 1.79 (m, 2H), 1.58 (m, 2H). MS: calculated for C24H26N4O+H 387.2; found: 387.3.

Sources & evidence

ORD record
ord-7fd6e5177d9c4fdda9f81f2e139022fb
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

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