5-[3-Fluoro-4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione → 5-(3-{1-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-2-fluoro-phenyl]-piperidin-4-ylamino}-(2S)-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C@@H:17]([OH:20])[CH2:18][NH2:19])[CH:13]=2)[NH:8][C:7]=1[CH3:21])=[O:5])[CH3:2].[F:22][C:23]1[CH:24]=[C:25]([CH:34]=[CH:35][C:36]=1[N:37]1[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]1)[CH2:26][CH:27]1[S:31][C:30](=[O:32])[NH:29][C:28]1=[O:33]>>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C@@H:17]([OH:20])[CH2:18][NH:19][CH:40]3[CH2:41][CH2:42][N:37]([C:36]4[CH:35]=[CH:34][C:25]([CH2:26][CH:27]5[S:31][C:30](=[O:32])[NH:29][C:28]5=[O:33])=[CH:24][C:23]=4[F:22])[CH2:38][CH2:39]3)[CH:13]=2)[NH:8][C:7]=1[CH3:21])=[O:5])[CH3:2]Participants
Reactant 2
Product 1
Procedure
The title compound was prepared from 5-((2S)-3-amino-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester (which was obtained in Example 141) and 5-[3-fluoro-4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 61) according to the procedure of Example 73 as a yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.34 (t, J=7.1 Hz, 3H), 1.56-1.63 (m, 2H), 2.03 (m, 2H), 2.61 (s, 3H), 2.67-2.75 (m, 4H), 2.88-2.96 (m, 4H), 3.04-3.07 (m, 2H), 3.95-3.97 (m, 2H), 4.05 (m, 2H), 4.25 (q, J=7.1 Hz, 2H), 4.61-4.66 (m, 1H), 5.52 (brs, 1H), 6.79 (dd, J=8.7, 2.5 Hz, 1H), 6.94-7.03 (m, 2H), 7.24-7.29 (m, 2H), 7.46 (d, J=2.3 Hz, 1H) 11.65 (s, 1H); MS (ES) m/z: 599.1 (MH+); HRMS for C30H36FN4O6S(MH+): 599.2339. Found: 599.2333.
Sources & evidence
- ORD record
- ord-48a25b214fae43a1912517259f50e524
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525202B2
Reaction notes
Loading…