1,2-Dichloroethane → 2-{[(4-Fluorophenyl)methyl]oxy}-N-3-pyridinyl-5-(trifluoromethyl)benzamide
Reaction equation
C(Cl)CCl.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][C:41]=2[C:42](O)=[O:43])=[CH:34][CH:33]=1>CN(C)C=O.O>[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]([F:50])([F:51])[F:52])=[CH:45][C:41]=2[C:42]([NH:11][C:7]2[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=2)=[O:43])=[CH:34][CH:33]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
EDC (122 mg, 0.64 mmol), 3-pyridinamine (59.9 mg, 0.64 mmol), HOBT (63.4 mg, 0.41 mmol) and diisopropylethylamine (0.11 ml, 0.64 mmol) were added to a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-(trifluoromethyl)benzoic acid (may be prepared as described in Description 119; 100 mg, 0.32 mmol) in N,N-dimethylformamide (5 ml) and the mixture was stirred at room temperature overnight. The mixture was then heated to 70° C. for 5 hours. The mixture was diluted with water (25 ml) and extracted with ethyl acetate (3×25 ml). The organics were combined, evaporated under reduced pressure on a buchi and the residue was purified using an MDAP to yield the title compound. 85 mg.
Workup
- temperatureThe mixture was then heated to 70° C. for 5 hours
- extractionextracted with ethyl acetate (3×25 ml)
- customevaporated under reduced pressure on a buchi
- customthe residue was purified
Sources & evidence
- ORD record
- ord-5844597a2bd646659164029c29ea405f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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