Trifluoroacetic acid → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(difluoromethyl)benzonitrile trifluoroacetate

HRID 1875207Notes

Reaction equation

HRID 1875207 reaction equation
CC([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][C:18]2[CH:23]=[C:22]([CH:24]([F:26])[F:25])[CH:21]=[C:20]([C:27]#[N:28])[CH:19]=2)[C:11]=1[F:29])C(=O)[O-])(C)C.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]>C(Cl)Cl>[F:33][C:32]([F:35])([F:34])[C:30]([OH:36])=[O:31].[NH2:5][CH2:9][C:10]1[C:11]([F:29])=[C:12]([O:17][C:18]2[CH:19]=[C:20]([CH:21]=[C:22]([CH:24]([F:26])[F:25])[CH:23]=2)[C:27]#[N:28])[C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867616571,1-Dimethylethyl[(4-chloro-3-{[3-cyano-5-(difluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]carbamate

Product 1

HCID 867616563-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(difluoromethyl)benzonitrile trifluoroacetateYield 84.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[(4-chloro-3-{[3-cyano-5-(difluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]carbamate (210 mg, 0.492 mmol) in DCM (10 ml) was added TFA (3.0 mL, 38.9 mmol) and the reaction mixture was stirred at RT for 30 minutes. The solvent was removed and the crude material 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(difluoromethyl)benzonitrile trifluoroacetate (183 mg, 0.415 mmol, 84% yield) was used directly in the next step without purification. 1H NMR

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-f23c34ec19ae43ba8089b6b413e7ceb5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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