4-[2-(Morpholine-4-sulfonyl)-ethyl]-phenylamine → 8-Indan-5-yl-2-{4-[2-(morpholine-4-sulfonyl)-ethyl]-phenylamino}-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester
Reaction equation
[N:1]1([S:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:19]([O:21][C:22]([C:24]1[C:25](=[O:48])[C:26]2[CH:31]=[N:30][C:29](S(CC)(=O)=O)=[N:28][C:27]=2[N:37]([C:39]2[CH:40]=[C:41]3[C:45](=[CH:46][CH:47]=2)[CH2:44][CH2:43][CH2:42]3)[CH:38]=1)=[O:23])[CH3:20]>>[CH2:19]([O:21][C:22]([C:24]1[C:25](=[O:48])[C:26]2[CH:31]=[N:30][C:29]([NH:18][C:15]3[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][S:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)(=[O:9])=[O:8])=[CH:13][CH:14]=3)=[N:28][C:27]=2[N:37]([C:39]2[CH:40]=[C:41]3[C:45](=[CH:46][CH:47]=2)[CH2:44][CH2:43][CH2:42]3)[CH:38]=1)=[O:23])[CH3:20]Participants
3
Reactant 2
Product 1
Procedure
Using the procedure outlined in Example 1(g) the title compound was prepared from 4-[2-(morpholine-4-sulfonyl)-ethyl]-phenylamine (65 mg, 0.24 mmol) and 8-indan-5-yl-2-ethanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(e) above, 100 mg, 0.24 mmol). The title compound was obtained as a white solid (42 mg, 29%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.35 (s, 1H), 8.53 (s, 1H), 8.01 (br, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.30 (m, 3H), 7.19 (d, J=7.8 Hz, 1H), 6.94 (br, 2H), 4.37 (q, J=7.1 Hz, 2H), 3.72 (t, J=4.5 Hz, 4H), 3.25 (t, J=4.7 Hz, 4H), 3.08 (m, 6H), 3.01 (t, J=7.4 Hz, 2H), 2.24 (m, 2H), 1.38 (t, J=7.1 Hz, 3H).
Sources & evidence
- ORD record
- ord-d278d560e6064cae8dcf8527262a24df
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642270B2
Reaction notes
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