2-Bromopyridine → N-[(3R,4S)-4-ethoxy-1-pyridin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-amine
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:10][C@H:11]1[CH2:15][NH:14][CH2:13][C@H:12]1[NH:16][C:17]1[C:22]([CH2:23][CH3:24])=[N:21][C:20]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[CH3:33])=[C:19]([CH2:34][CH3:35])[N:18]=1)[CH3:9]>>[CH2:8]([O:10][C@H:11]1[CH2:15][N:14]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:13][C@H:12]1[NH:16][C:17]1[C:22]([CH2:23][CH3:24])=[N:21][C:20]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[CH3:33])=[C:19]([CH2:34][CH3:35])[N:18]=1)[CH3:9]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-diethylpyrzin-2-amine but substituting 2-bromopyridine and starting with N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.15, 1.31, 2.14, 2.49, 2.71, 3.42, 3.54, 3.78, 3.85, 4.07, 4.28, 4.92, 5.21, 6.50˜6.66, 6.79, 6.84, 7.12, 8.20; IR (diffuse reflectance) 2969, 2405 (w), 2351 (w), 2337 (w), 2212 (w), 2015 (w), 1599 (s), 1560, 1482 (s), 1474 (s), 1442 (s), 1392, 1385, 1242, 769 cm−1 HRMS (ESI) calcd for C27H35N5O2+H1 462.2869. found 462.2859.
Sources & evidence
- ORD record
- ord-6e8dd050f7cf4b9d9d711faca1167a8c
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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