Dipropylamine → N-(3-(trifluoromethyl)benzyl)-2-(5-(dipropylamino)-2-nitrophenyl)isonicotinamide
Reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].C(N(CC)C(C)C)(C)C.[F:17][C:18]([F:46])([F:45])[C:19]1[CH:20]=[C:21]([CH:42]=[CH:43][CH:44]=1)[CH2:22][NH:23][C:24](=[O:41])[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31]2[CH:36]=[C:35](F)[CH:34]=[CH:33][C:32]=2[N+:38]([O-:40])=[O:39])[CH:26]=1>CN(C)C=O.O>[F:17][C:18]([F:45])([F:46])[C:19]1[CH:20]=[C:21]([CH:42]=[CH:43][CH:44]=1)[CH2:22][NH:23][C:24](=[O:41])[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31]2[CH:36]=[C:35]([N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])[CH:34]=[CH:33][C:32]=2[N+:38]([O-:40])=[O:39])[CH:26]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Into a 10-mL vial, was placed a solution of dipropylamine (216.9 mg, 2.15 mmol, 3.00 equiv) in N,N-dimethylformamide (3 mL), N,N-diisopropylethylamine (277 mg, 2.15 mmol, 3.00 equiv), and a solution of N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide 14d (300 mg, 0.72 mmol, 1.00 equiv) in N,N-dimethylformamide (2 mL). The resulting solution was stirred for 8 h at 90° C. to 100° C. in an oil bath. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×70 mL of brine, dried over sodium sulfate, and concentrated under vacuum. The crude product was obtained as 400 mg of a yellow to green oil.
Workup
- extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
- washThe resulting mixture was washed with 2×70 mL of brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-db095809d5be489bbce593270f1a8a2b
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301951B2
Reaction notes
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