Trifluoroacetic acid → HCID 68487554, compound

HRID 1875181Notes

Reaction equation

HRID 1875181 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]3[CH2:26][CH2:25]3)[CH:21]=[C:20]([C:27]#[N:28])[CH:19]=2)[C:11]=1[F:29])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCOC(C)=O>[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]3[CH2:25][CH2:26]3)[CH:23]=2)[C:27]#[N:28])[C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86761654HCID 86761654, compound

Product 1

HCID 68487554HCID 68487554, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)carbamate (880 mg, 2.111 mmol) dissolved in DCM (15 ml) was added TFA (5.0 ml) and the reaction mixture was stirred for 30 minutes at RT. The reaction mixture was neutralized with saturated sodium bicarbonate, diluted with EtOAc, and the organics layer was separated. The solvent was evaporated and the crude material was purifed via silica gel chromatography to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-cyclopropylbenzonitrile (594 mg, 1.875 mmol, 89% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.38-7.52 (m, 2H), 7.22 (s, 1H), 7.04 (d, 2H), 3.73 (s, 2H), 1.91-2.01 (m, 1H), 1.89 (br. s., 2H), 0.89-1.04 (m, 2H), 0.64-0.81 (m, 2H).

Workup

  1. customthe organics layer was separated
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-05aeee70b58041aebe21529220920975
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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