(S)-4-(4-Aminobenzyl)oxazolidin-2-one → (4S)-8-Indan-5-yl-5-oxo-2-[4-(2-oxo-oxazolidin-4-ylmethyl)-phenylamino]-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 1989037Notes

Reaction equation

HRID 1989037 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18]([C:20]1[C:21](=[O:43])[C:22]2[CH:27]=[N:26][C:25](S(C)(=O)=O)=[N:24][C:23]=2[N:32]([C:34]2[CH:35]=[C:36]3[C:40](=[CH:41][CH:42]=2)[CH2:39][CH2:38][CH2:37]3)[CH:33]=1)=[O:19])[CH3:16]>>[CH2:15]([O:17][C:18]([C:20]1[C:21](=[O:43])[C:22]2[CH:27]=[N:26][C:25]([NH:1][C:2]3[CH:14]=[CH:13][C:5]([CH2:6][C@H:7]4[CH2:11][O:10][C:9](=[O:12])[NH:8]4)=[CH:4][CH:3]=3)=[N:24][C:23]=2[N:32]([C:34]2[CH:35]=[C:36]3[C:40](=[CH:41][CH:42]=2)[CH2:39][CH2:38][CH2:37]3)[CH:33]=1)=[O:19])[CH3:16]

Participants

3

Reactant 2

HCID 7099156(S)-4-(4-Aminobenzyl)oxazolidin-2-oneHCID 252229828-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 68676883(4S)-8-Indan-5-yl-5-oxo-2-[4-(2-oxo-oxazolidin-4-ylmethyl)-phenylamino]-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Procedure

Using the procedure outlined in Example 1(g) the title compound was prepared from (4S)-4-(4-amino-benzyl)-1,3-oxazolidin-2-one (46 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 (56 mg, 44%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.00 (br, 1H), 8.42 (s, 1H), 7.50 (br, 1H), 7.33 (d, J=7.9 Hz, 1H), 7.28 (br, 2H), 7.18 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.81 (br, 2H), 5.88 (s, 1H), 4.41 (t, J=8.2 Hz, 1H), 4.31 (q, J=7.0 Hz, 2H), 4.05 (m, 1H), 3.98 (m, 1H), 2.99 (t, J=7.4 Hz, 2H), 2.92 (t, J=7.4 Hz, 2H), 2.79-2.66 (m, 2H), 2.15 (m, 2H), 1.31 (t, J=7.1 Hz, 3H).

Sources & evidence

ORD record
ord-788d028d0ea34cd09912eb9cf9b2f138
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

Loading…