Isopropylamine → 5-chloro-N-(propan-2-yl)pyrazine-2-carboxamide
Reaction equation
[CH:1]([N:4](CC)C(C)C)([CH3:3])[CH3:2].[Cl:10][C:11]1[N:12]=[CH:13][C:14]([C:17]([OH:19])=O)=[N:15][CH:16]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CC(N)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:10][C:11]1[N:12]=[CH:13][C:14]([C:17]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:19])=[N:15][CH:16]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
N,N-Diisopropylethylamine (2.6 mL, 15 mmol) was added to a mixture of 5-chloropyrazine-2-carboxylic acid (0.80 g, 5.0 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.46 g, 5.56 mmol) and 2-propanamine (0.47 mL, 5.6 mmol) in methylene chloride (20 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was worked up with sat. aqueous NaHCO3, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with ethyl acetate in hexanes (0-15%) to afford the desired product. LCMS cacld. for C8H11ClN3O (M+1)+: m/z=200.1. Found: 200.1.
Workup
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography on a silica gel column
- washeluting with ethyl acetate in hexanes (0-15%)
Sources & evidence
- ORD record
- ord-ec2d5e6d79e1435bb3d1a8f75ea6bfab
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382231B2
Reaction notes
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