8-Cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester → 8-Cyclohexyl-2-{4-[1-(2-dimethylamino-acetyl)-piperidin-4-yl]-phenylamino}-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester
Reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].[CH2:20]([O:22][C:23]([C:25]1[C:26](=[O:45])[C:27]2[CH:32]=[N:31][C:30](S(C)(=O)=O)=[N:29][C:28]=2[N:37]([CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[CH:38]=1)=[O:24])[CH3:21]>>[CH2:20]([O:22][C:23]([C:25]1[C:26](=[O:45])[C:27]2[CH:32]=[N:31][C:30]([NH:18][C:15]3[CH:14]=[CH:13][C:12]([CH:9]4[CH2:8][CH2:7][N:6]([C:4](=[O:5])[CH2:3][N:2]([CH3:19])[CH3:1])[CH2:11][CH2:10]4)=[CH:17][CH:16]=3)=[N:29][C:28]=2[N:37]([CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[CH:38]=1)=[O:24])[CH3:21]Participants
3
Reactant 2
Product 1
Procedure
Using the procedure outlined in Example 1(g) the title compound was prepared from 4-[1-(2-dimethylamino-acetyl)-piperidin-4-yl]-phenylamine (from Example 70(B)), 73 mg, 0.28 mmol) and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 17(e), 100 mg, 0.26 mmol). The title compound was obtained as a white solid (40 mg, 25%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.21 (s, 1H), 8.99 (s, 1H), 8.41 (s, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.13 (d, J=8.5 Hz, 2H), 4.96 (m, 3H), 4.31 (q, J=7.1 Hz, 2H), 3.00 (m, 4H), 2.77 (m, 1H), 2.30 (s, 6H), 1.93 (m, 6H), 1.64 (m, 5H), 1.42 (m, 2H), 1.34 (t, J=7.1 Hz, 3H), 1.18(m, 1H).
Sources & evidence
- ORD record
- ord-ff3b1a5eb9874d9c927bf2a10556e7ba
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642270B2
Reaction notes
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