8-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester → 8-Indan-5-yl-2-[4-(2-isopropylsulfamoyl-ethyl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester
Reaction equation
[CH:1]([NH:4][S:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[CH2:17]([O:19][C:20]([C:22]1[C:23](=[O:45])[C:24]2[CH:29]=[N:28][C:27](S(C)(=O)=O)=[N:26][C:25]=2[N:34]([C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)[CH2:41][CH2:40][CH2:39]3)[CH:35]=1)=[O:21])[CH3:18]>>[CH2:17]([O:19][C:20]([C:22]1[C:23](=[O:45])[C:24]2[CH:29]=[N:28][C:27]([NH:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][S:5](=[O:7])(=[O:6])[NH:4][CH:1]([CH3:3])[CH3:2])=[CH:15][CH:14]=3)=[N:26][C:25]=2[N:34]([C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)[CH2:41][CH2:40][CH2:39]3)[CH:35]=1)=[O:21])[CH3:18]Participants
3
Reactant 2
Product 1
Procedure
Using the procedure outlined in Example 1(g) the title compound was prepared from 2-(4-amino-phenyl)-ethanesulfonic acid isopropylamide (58 mg, 0.24 mmol) and 8-indan-5-yl-2-methanesulfonyl-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 (50 mg, 36%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.34 (s, 1H), 8.53 (s, 1H), 7.88 (br, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.27 (m, 3H), 7.18 (d, J=7.9 Hz, 1H), 6.94 (br, 2H), 5.88 (s, 1H), 4.37 (q, J=7.1 Hz, 2H), 3.61 (m, 1H), 3.22 (m, 2H), 3.10-2.96 (m, 6H), 2.23 (m, 2H), 1.38 (t, J=7.1 Hz, 3H), 1.25 (s, 3H), 1.22 (s, 3H).
Sources & evidence
- ORD record
- ord-2f58f47c72eb4e7892f3d4738af8a515
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642270B2
Reaction notes
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