Propionyl chloride → 5-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxy-1-propionylpyrrolidin-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])[CH3:2].[C:31](Cl)(=O)CC>>[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](=[O:3])[CH2:2][CH3:31])[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 propionyl chloride and making non-critical variations provided the title compound as an oil: 1H NMR (400 MHz, DMSO) δ) 7.71, 7.50, 7.41, 6.00, 5.98, 4.68, 4.52, 4.22, 4.11, 3.85-3.39, 2.68, 2.37, 2.25, 1.24-0.85; HRMS (FAB) calcd for C23H30Cl2N4O2+H 465.1824, found 465.1825.
Sources & evidence
- ORD record
- ord-d299139f1bcd4d778526075953d03c11
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06992087B2
Reaction notes
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