4-Bromopyridine → 5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-pyridin-4-ylpyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:31][CH3:32])[C:12]([NH:17][C@H:18]2[C@@H:22]([O:23][CH2:24][CH3:25])[CH2:21][N:20]([C:26]3SC=CN=3)[CH2:19]2)=[N:13][C:14]=1[CH2:15][CH3:16].BrC1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:31][CH3:32])[C:12]([NH:17][C@H:18]2[C@@H:22]([O:23][CH2:24][CH3:25])[CH2:21][N:20]([C:26]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH2:19]2)=[N:13][C:14]=1[CH2:15][CH3:16]Participants
3
Procedure
Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine but substituting 4-bromo pyridine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ) 8.23, 7.50, 7.35, 7.28, 6.50, 5.30, 4.90, 4.29, 3.95, 3.76, 3.65–3.58, 3.42, 2.73, 2.49, 1.35–1.27, 1.16; IR (diffuse reflectance) 2971 (s), 2497 (w), 2388 (w), 2350 (w), 2338 (w), 2328 (w), 1596 (s), 1569, 1550 (s), 1516, 1508, 1499 (s), 1467 (s), 1397 (s), 1393 (s) cm−1 HRMS (ESI) calcd for C25H29N5OCl2+H1 486.1827. found 486.1810.
Sources & evidence
- ORD record
- ord-c4387b128ed74edf87e4c3ea247df0f9
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
Loading…