1-Bromo-3-chloropropane → 3-[3-{2-[2-(3-Chloropropoxy)phenyl]pyrrolidin-1-yl}-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-4-methylbenzamide
Reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:18]=[CH:17][NH:16][CH:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH:20]4[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[OH:30])[C:14]3=[O:31])[CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][CH2:41][CH2:42][Cl:43]>C(#N)C.O>[Cl:43][CH2:42][CH2:41][CH2:40][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:15]1[C:14](=[O:31])[N:13]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=2[CH3:12])[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:32])[CH:18]=[CH:17][N:16]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 83 °C
Procedure
A solution of N-cyclopropyl-3-{3-[2-(2-hydroxyphenyl)pyrrolidin-1-yl]-2-oxo-3,4-dihydropyrazin-1(2H)-yl}-4-methylbenzamide (Example 324a, 0.2 g) in acetonitrile (5 mL) was treated with potassium carbonate (0.642 g) and 1-bromo-3-chloropropane (0.459 mL) under nitrogen. The resulting suspension was stirred at 83° C. for 10 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and evaporated to give the subtitle compound (0.23 g).
Workup
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-f8f4e183f46047bdacb3b21d4d747f2f
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163905B2
Reaction notes
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