3-Bromopyridine → 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxy-1-pyridin-3-ylpyrrolidin-3-yl]-3,6-diethyl pyrazin-2-amine
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[C:17]1[N:18]=[C:19]([CH2:34][CH3:35])[C:20]([NH:25][C@H:26]2[C@@H:30]([O:31][CH2:32][CH3:33])[CH2:29][NH:28][CH2:27]2)=[N:21][C:22]=1[CH2:23][CH3:24]>>[Cl:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[C:17]1[N:18]=[C:19]([CH2:34][CH3:35])[C:20]([NH:25][C@H:26]2[C@@H:30]([O:31][CH2:32][CH3:33])[CH2:29][N:28]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[CH2:27]2)=[N:21][C:22]=1[CH2:23][CH3:24]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 3-bromopyridine and starting with 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.17, 1.26–1.33, 2.51, 2.73, 3.39, 3.57, 3.76, 3.78, 3.86, 3.93, 4.31, 4.91, 5.26, 6.89, 7.04, 7.25, 8.00; IR (diffuse reflectance) 2970, 2430 (w), 2054 (w), 1914 (w), 1603, 1584, 1566 (s), 1481 (s), 1434, 1396, 1372, 1287, 1228, 1122, 1044 cm−1 HRMS (ESI) calcd for C26H32N5O2Cl+H1 482.2322. found 482.2311.
Sources & evidence
- ORD record
- ord-af183aa16bf2415d8df38dbc1ebd9821
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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