Triethylamine → 4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide
Reaction equation
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36].C(N(CC)CC)C.N[C:46]1[CH:47]=[C:48]([CH3:55])[C:49](C)([CH3:53])[NH:50][C:51]=1C>CN(C=O)C>[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:2][C:51]2[CH:46]=[CH:47][C:48]([CH3:55])=[C:49]([CH3:53])[N:50]=2)=[O:32])=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To DMF (20 mL) were added HATU (2.87 g, 7.55 mmol), 4-amino-3-nitrobenzoic acid (916 mg, 5.03 mmol), triethylamine (1.05 mL, 762 mmol) and 5-amino-2,3-dimethyllutidine (615 mg, 5.03 mmol) [J. Het. Chem. 31, 1641 (1994)]. The mixture was stirred at ambient temperature for 1 h, then at 80° C. for 18 h. The solution was decanted into ethyl acetate and extracted once with water and five times with brine, then dried, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography using a gradient of 80-100% heptane/ethyl acetate to give 4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide. MS (m/z) 287.0 (M+1).
Workup
- waitat 80° C. for 18 h
- customThe solution was decanted into ethyl acetate
- extractionextracted once with water and five times with brine
- customdried
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe residue was purified by chromatography
Sources & evidence
- ORD record
- ord-8ef9ed8c2983408895d88b71b23fcab6
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222248B2
Reaction notes
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