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

HRID 1376232Notes

Reaction equation

HRID 1376232 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=O)[NH:18][C:19]2[C:20](=[O:31])[N:21]([CH3:30])[C:22]3[C:27]([C:28]=2[NH2:29])=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>>[CH2:1]([O:8][C:9](=[O:33])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[NH:18][C:19]3[C:20](=[O:31])[N:21]([CH3:30])[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:28]=3[N:29]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 45123293[3-(4-Amino-1-methyl-2-oxo-1,2-dihydro-quinolin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

Product 1

HCID 58788441[3-(5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-cyclohexyl]-carbamic acid benzyl esterYield 92.4%

Procedure

As described in example 3D, [3-(4-amino-1-methyl-2-oxo-1,2-dihydro-quinolin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester (0.22 g, 0.49 mmol) was heated in glacial acetic acid (5.30 g, 88.3 mmol) to give [3-(5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-cyclohexyl]-carbamic acid benzyl ester (0.195 g, 92% yield). 1H-NMR (CDCl3): δ 8.18 (m, 1H), 7.51 (m, 2H), 7.34 (m, 7H), 5.10 (s, 2H), 3.84 (s, 3H), 2.48 (m, 1H), 2.17 (m, 3H), 1.92 (m, 1H), 1.72 (m, 3H), 1.53 (m, 1H), 1.13 (m, 2H). MS: calculated for C25H26N4O3+H 431.2; found: 431.0.

Sources & evidence

ORD record
ord-392ff50e97fc41b89b1373018a9b9cd7
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

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