2-Bromopyrimidine → N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]pyrazin-2-amine
Reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H]2[C@@H](OCC)CN(C3SC=CN=3)C2)=NC=1CC.Br[C:34]1[N:39]=[CH:38][CH:37]=[CH:36][N:35]=1.[CH2:40]([O:42][C@H:43]1[CH2:47][NH:46][CH2:45][C@H:44]1[NH:48][C:49]1[C:54]([CH2:55][CH3:56])=[N:53][C:52]([C:57]2[C:58]([C:65]([F:68])([F:67])[F:66])=[N:59][C:60]([O:63][CH3:64])=[CH:61][CH:62]=2)=[C:51]([CH2:69][CH3:70])[N:50]=1)[CH3:41]>>[CH2:40]([O:42][C@H:43]1[CH2:47][N:46]([C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:45][C@H:44]1[NH:48][C:49]1[C:54]([CH2:55][CH3:56])=[N:53][C:52]([C:57]2[C:58]([C:65]([F:68])([F:67])[F:66])=[N:59][C:60]([O:63][CH3:64])=[CH:61][CH:62]=2)=[C:51]([CH2:69][CH3:70])[N:50]=1)[CH3:41]Participants
4
Reactant 3
Product 1
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 2-bromopyrimidine and starting with N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]pyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.15, 1.30, 2.43, 2.69, 3.53, 3.78, 3.87, 3.99, 4.04, 4.27, 4.91, 5.27, 6.61, 6.97, 7.56, 8.41; IR (diffuse reflectance) 2398 (w), 2352 (w), 2307 (w), 2214 (w), 2173 (w), 1584 (s), 1569, 1549 (s), 1508 (s), 1476 (s), 1397, 1341, 1277, 1175, 1137 (s) cm−1 HRMS (ESI) calcd for C25H30N7O2F3+H1 518.2491. found 518.2479.
Sources & evidence
- ORD record
- ord-09c69188d6c44b18aab320b53046957e
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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