Trifluoroacetic anhydride → HCID 59004196, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=1.[O:18](C(C(F)(F)F)=O)[C:19]([C:21]([F:24])([F:23])[F:22])=O>FC(F)(F)C(O)=O>[F:22][C:21]([F:23])([F:24])[C:19]([NH:17][C:14]1[CH:13]=[CH:12][C:11]([N:10]2[C:3]3[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=3[N:1]=[C:19]2[C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=1)=[O:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of N5-(2-Amino-4-methoxy-phenyl)-pyridine-2,5-diamine (150 mg, 0.65 mmol) in trifluoroacetic acid (5 ml) was added (CF3CO)2O (5 ml). The resultant solution was allowed to stir at 80° C. for 4 hours. The reaction progress was monitored by TLC (EtOAc/petroleum ether=1:2). The mixture was concentrated under reduced pressure on a rotary evaporator. The reaction mixture was then quenched by adding 30 ml of 10% NaHCO3. The resultant solution was extracted three times with 50 ml of EtOAc and the organic layers were combined and dried over Na2SO4. After removal of the drying reagent by filtration, the crude product, 2,2,2-Trifluoro-N-[5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyridin-2-yl]-acetamide (ff), was obtained by removal of the solvent under reduced pressure and it was used directly in the next step without purification.
Workup
- concentrationThe mixture was concentrated under reduced pressure on a rotary evaporator
- customThe reaction mixture was then quenched
- additionby adding 30 ml of 10% NaHCO3
- extractionThe resultant solution was extracted three times with 50 ml of EtOAc
- dry with materialdried over Na2SO4
- customAfter removal of the drying reagent
- filtrationby filtration
Sources & evidence
- ORD record
- ord-a58991fa590b49e1a4f32ac78ac38c68
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163777B2
Reaction notes
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