Triethylamine → 2-{[3-Cyano-4-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate
Reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:17]([F:20])([F:19])[F:18])=[C:13]([CH:16]=1)[C:14]#[N:15].[C:21]([O:24][CH2:25][C:26](Cl)=[O:27])(=[O:23])[CH3:22]>C(Cl)Cl>[C:21]([O:24][CH2:25][C:26]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:17]([F:18])([F:19])[F:20])=[C:13]([C:14]#[N:15])[CH:16]=1)=[O:27])(=[O:23])[CH3:22]Participants
5
Procedure
Triethylamine (1.09 g, 10.8 mmol) was added to a stirred solution of 5-amino-2-(trifluoromethyl)benzonitrile (Intermediate 37, 1.0 g, 5.37 mmol) in DCM (40 mL), at 0° C., and the mixture was stirred for 15 min. Chloro-2-oxoethyl acetate (1.10 g, 8.06 mmol) was added at 0° C. and the mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with DCM and washed with ice water, and saturated brine solution. The organic layer was dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-40% EtOAc/pet.ether to give the title compound (1.1 g).
Workup
- stirringthe mixture was stirred for 4 h at room temperature
- washwashed with ice water, and saturated brine solution
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customto afford the crude compound
- customThis was purified by column chromatography (100-200 mesh silica gel)
- washeluting with 20%-40% EtOAc/pet
Sources & evidence
- ORD record
- ord-a39cd9a1d76e4c3b9fcd57eb7ecc80ca
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
Loading…