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
Reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[NH:31][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)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CCO.[Pd]>[CH2:19]([N:31]1[C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=3[C:19]=2[N:18]=[C:17]1[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)[C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Sources & evidence
- ORD record
- ord-1e8984e76d634d2aa45d0996396b43ec
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678909B1
Reaction notes
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