2-Chloro-4-methoxypyridine → 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxy-1-(4-methoxypyridin-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine hydrogen chloride
Reaction equation
[Cl:1]C1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H:18]2[C@@H:22]([O:23][CH2:24]C)[CH2:21][N:20]([C:26]3SC=CN=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].ClC1C=C(OC)C=CN=1>>[ClH: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:19]3[CH:18]=[C:22]([O:23][CH3:24])[CH:21]=[CH:26][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-methoxypyridine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ 8.6, 8.08, 7.22, 7.12, 7.05, 6.90, 6.40, 5.92, 5.40, 5.00, 4.32, 4.20–4.10, 3.95, 3.86, 3.52, 2.81, 2.60, 1.33, 1.26, 1.18; IR (diffuse reflectance) 2966, 2934, 2685 (b), 2036 (w), 1974 (w), 1657, 1607 (s), 1493, 1463, 1442, 1404, 1293, 1265, 1232, 826 cm−1 HRMS (ESI) calcd for C27H34N5O3Cl+H1 512.2429. found 512.2417.
Sources & evidence
- ORD record
- ord-5ec54b1302024e39a32bbb6a160180e6
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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