2-Chloro-4-methoxypyrimidine → 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxy-1-(4-methoxypyrimidin-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine
Reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H:18]2[C@@H:22]([O:23][CH2:24]C)C[N:20]([C:26]3SC=C[N:30]=3)[CH2:19]2)=NC=1CC.[Cl:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[C:42]1[N:43]=[C:44]([CH2:59][CH3:60])[C:45]([NH:50][C@H:51]2[C@@H:55]([O:56][CH2:57][CH3:58])[CH2:54][NH:53][CH2:52]2)=[N:46][C:47]=1[CH2:48][CH3:49].ClC1N=C(OC)C=CN=1>>[Cl:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[C:42]1[N:43]=[C:44]([CH2:59][CH3:60])[C:45]([NH:50][C@H:51]2[C@@H:55]([O:56][CH2:57][CH3:58])[CH2:54][N:53]([C:26]3[N:30]=[C:22]([O:23][CH3:24])[CH:18]=[CH:19][N:20]=3)[CH2:52]2)=[N:46][C:47]=1[CH2:48][CH3:49]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 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine and 2-chloro-4-methoxypyrimidine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ) 8.03, 7.25, 7.02, 6.90, 6.02, 5.25, 4.88, 4.22, 3.92–3.78, 3.55, 2.74, 2.50, 1.33–1.26, 1.16; IR (diffuse reflectance) 2972, 2475 (w), 2350 (w), 2310 (w), 2183 (w), 2069 (w), 1585 (s), 1568 (s), 1516 (s), 1482 (s), 1466 (s), 1397, 1393, 1292, 1231 cm−1 HRMS (ESI) calcd for C26H33N6O3Cl+H1 513.2380. found 513.2356.
Sources & evidence
- ORD record
- ord-b5bf9ac390954eafa7ac777529e4aa71
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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