Trifluoroacetic acid → HCID 77845072, compound

HRID 1484196Notes

Reaction equation

HRID 1484196 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][C:8]=2[C:9]([NH:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:14][CH:13]=2)=[O:10])=[C:4]([CH3:35])[CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][C:8]=2[C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:23][CH:24]=2)=[O:10])=[C:4]([CH3:35])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90315065HCID 90315065, compound

Product 1

HCID 77845072HCID 77845072, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[[2-(4-fluoro-2-methyl-phenoxy)-5-(trifluoromethyl)benzoyl]amino]benzoate (43.8 mg, 0.09 mmol) was suspended in dichloromethane (1.45 mL) and TFA (1.45 mL) was added and the mixture stirred 0.5 h at room temperature. The reaction mixture was filtered and purified by reverse phase HPLC using a gradient of acetonitrile and water (10-99%) and HCl as a modifier to yield 4-(2-(4-fluoro-2-methylphenoxy)-5-(trifluoromethyl)benzamido)benzoic acid (28) (24.71 mg, 67%). ESI-MS m/z calc. 433.09. found 434.3 (M+1)+; Retention time: 2.00 minutes (3 minutes run). 1H NMR (400 MHz, DMSO) δ 12.78 (s, 1H), 10.83 (s, 1H), 8.01 (d, J=2.1 Hz, 1H), 7.94 (d, J=8.7 Hz, 2H), 7.80 (dd, J=15.4, 5.6 Hz, 3H), 7.18 (m, 3H), 6.83 (d, J=8.7 Hz, 1H), 2.14 (s, 3H) ppm.

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-e118308ad1474e7a99b9529359a0e176
Source dataset
uspto-grants-2016_08
Patent number
US09421196B2

Reaction notes

Loading…