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-(4-methoxy-2-methylphenyl)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[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][C:51]=2[CH3:58])=[C:44]([CH2:59][CH3:60])[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[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][C:51]=2[CH3:58])=[C:44]([CH2:59][CH3:60])[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-(4-methoxy-2-methylphenyl)pyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.15, 1.31, 2.13, 2.47, 2.71, 3.45˜3.59, 3.77, 3.85, 4.03, 4.28, 4.93, 5.21, 6.54, 6.81, 6.83, 7.11, 7.26; IR (diffuse reflectance) 2970, 2932, 2403 (w), 2350 (w), 2334 (w), 2212 (w), 1965 (w), 1608, 1537 (s), 1482 (s), 1393, 1294, 1242, 1200, 1165 cm−1 HRMS (ESI) calcd for C25H33N5O2S+H1 468.2433. found 468.2416.
Sources & evidence
- ORD record
- ord-931cf87f954043b5b20f1c701721a2dd
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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