5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine → N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-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([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)C2)=NC=1CC.[CH2:33]([O:35][C@H:36]1[CH2:40][NH:39][CH2:38][C@H:37]1[NH:41][C:42]1[C:47]([CH2:48][CH3:49])=[N:46][C:45]([C:50]2[C:51]([C:58]([F:61])([F:60])[F:59])=[N:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=2)=[C:44]([CH2:62][CH3:63])[N:43]=1)[CH3:34]>>[CH2:33]([O:35][C@H:36]1[CH2:40][N:39]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[CH2:38][C@H:37]1[NH:41][C:42]1[C:47]([CH2:48][CH3:49])=[N:46][C:45]([C:50]2[C:51]([C:58]([F:61])([F:60])[F:59])=[N:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=2)=[C:44]([CH2:62][CH3:63])[N:43]=1)[CH3:34]Participants
3
Reactant 2
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 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, 2.45, 2.68, 3.48˜3.58, 3.77, 3.88, 4.04, 4.29, 4.94, 5.29, 6.56, 6.98, 7.56; IR (diffuse reflectance) 2974, 2350 (w), 2337 (w), 1921 (w), 1607, 1568, 1538 (s), 1477 (s), 1397, 1342, 1278 (s), 1239, 1192, 1175, 1137 (s) cm−1 HRMS (ESI) calcd for C24H29N6O2SF3+H1 523.2103. found 523.2108.
Sources & evidence
- ORD record
- ord-4b629cf803fe4b598abc9cd3919c37fd
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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