4-(5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-piperidine-1-carboxylic acid benzyl ester → 3-Benzyl-5-methyl-2-piperidin-4-yl-3,5-dihydro-imidazo[4,5-c]quinolin-4-one

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Reaction Steps

As described in example 3F, a solution of 4-(5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-piperidine-1-carboxylic acid benzyl ester (43 mg, 0.085 mmol) in EtOH was hydrogenated over 10% Pd/C (41 mg, 0.038 mmol) at 1 atm to give 3-benzyl-5-methyl-2-piperidin-4-yl-3,5-dihydro-imidazo[4,5-c]quinolin-4-one (30 mg, 95%). A solution of the amine in EtOAc was treated with HCl (1 M in diethyl ether) to prepare the HCl salt. 1H-NMR (DMSO): δ 8.12 (d, 1H, J=6.4 Hz), 7.57 (m, 2H), 7.30 (m, 3H), 7.24 (m, 1H), 7.14 (m, 2H), 5.86 (s, 2H), 4.08 (m, 1H), 3.67 (s, 3H), 3.31 (m, 3H), 2.93 (m, 2H), 2.0 (m, 2H) 1.71 (m, 2H). MS: calculated for C23H24N4O+H 373.2; found: 373.3.

Provenance & Evidence