4-Morpholinecarbonyl chloride → 5-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxy-1-(morpholin-4-ylcarbonyl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine
Reaction equation
[C:1]([N:4]1[CH2:8][C@H:7]([O:9][CH2:10][CH3:11])[C@H:6]([NH:12][C:13]2[C:18]([CH2:19][CH3:20])=[N:17][C:16]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH2:5]1)(=[O:3])C.[N:31]1(C(Cl)=O)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:16]1[N:17]=[C:18]([CH2:19][CH3:20])[C:13]([NH:12][C@H:6]2[C@@H:7]([O:9][CH2:10][CH3:11])[CH2:8][N:4]([C:1]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:3])[CH2:5]2)=[N:14][C:15]=1[CH2:29][CH3:30]Participants
3
Procedure
Following the procedure for the preparation of N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine but substituting 4-morpholinecarbonyl chloride and making non-critical variations provided the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ) 7.50, 7.34, 7.28, 5.23, 4.69, 4.10, 3.90, 3.80-3.68, 3.58-3.28, 2.70, 2.49, 1.33-1.26, 1.16; IR (liq.) 2970 (s), 2934 (s), 2874 (s), 2353 (w), 1996 (w), 1956 (w), 1642 (s), 1567 (s), 1552 (s), 1500 (s), 1469 (s), 1414 (s,b), 1397 (s), 1118 (s), 1102 (s), cm−1HRMS (FAB) calcd for C25H33Cl2N5O3+H 522.2039, found 522.2038.
Sources & evidence
- ORD record
- ord-972a6bb56a46454abd43306549f8d242
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06992087B2
Reaction notes
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