Trifluoroacetic acid → HCID 10071678, compound

HRID 750994Notes

Reaction equation

HRID 750994 reaction equation
[F:1][CH:2]([F:35])[O:3][C:4]1[CH:5]=[C:6]([N:14]([CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[C:15]2[CH:27]=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[CH:17][CH:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].FC(F)(F)C(O)=O>ClCCl>[F:35][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([N:14]([CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:26][CH:27]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68953318HCID 68953318, compound

Product 1

HCID 10071678HCID 10071678, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution consisting of 1.75 g (3.44 mmol) of tert-butyl N-(3,4-bis-difluoromethoxyphenyl)-N-(3-pyridylmethyl)-4-aminobenzoate, 33.5 mL of dichloromethane and 8.4 mL of trifluoroacetic acid was stirred at room temperature for 5 hours. The solution was washed with 50 mL of H2O. Then 50 mL of H2O was added and the pH adjusted to 6 by the addition of 10% aqueous NaOH. The combined aqueous layers were extracted with 2×50 mL of dichloromethane. The combined dichloromethane extracts were evaporated and the remaining material was purified by flash chromatography over SiO2 using 10% MeOH in CH2Cl2 as eluant. The material was triturated with CH3CN to yield 1.09 g (73% yield) of the title compound as a white crystalline powder. [MW 436.359; ESMS m/z (M+H)+].

Workup

  1. washThe solution was washed with 50 mL of H2O
  2. additionThen 50 mL of H2O was added
  3. additionthe pH adjusted to 6 by the addition of 10% aqueous NaOH
  4. extractionThe combined aqueous layers were extracted with 2×50 mL of dichloromethane
  5. customThe combined dichloromethane extracts were evaporated
  6. customthe remaining material was purified by flash chromatography over SiO2 using 10% MeOH in CH2Cl2 as eluant
  7. customThe material was triturated with CH3CN

Sources & evidence

ORD record
ord-25f43a770da2468395c1f9a72b1baf34
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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