Water → 2-(2-(4-Chloro-1-methyl-1H-pyrazol-5-yl)-4-(3-(trifluoromethyl)benzamido)phenoxy)acetic Acid

HRID 1191625Notes

Reaction equation

HRID 1191625 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:35])[C:6]=1[C:7]1[CH:21]=[C:20]([NH:22][C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH:19]=[CH:18][C:8]=1[O:9][CH2:10][C:11]([O:13]C(C)(C)C)=[O:12].O.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:35])[C:6]=1[C:7]1[CH:21]=[C:20]([NH:22][C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=2)[CH:19]=[CH:18][C:8]=1[O:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67265312tert-Butyl 2-(2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-(3-(trifluoromethyl)benzamido)phenoxy)acetate

Product 1

HCID 672652962-(2-(4-Chloro-1-methyl-1H-pyrazol-5-yl)-4-(3-(trifluoromethyl)benzamido)phenoxy)acetic AcidYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-(3-(trifluoromethyl)benzamido)phenoxy)acetate (0.460 g, 0.902 mmol) in CH2Cl2 (5 mL) was added water (0.5 mL) and trifluoroacetic acid (5 mL, 56 mmol). The resulting solution was stirred for 18 hours, reduced under vacuum, azeotroped with toluene, and triturated in ether to give the title compound as a white solid (0.290 g, 70.8%). LCMS m/z (%)=454 (M+H, 35Cl, 100), 456(M+H, 37Cl, 30). 1H NMR (400 MHz, DMSO-d6) δ 3.72 (s, 3H) 4.70-4.84 (m, 2H) 7.11 (d, J=9.09 Hz, 1H) 7.63 (s, 1H) 7.72 (d, J=2.53 Hz, 1H) 7.79 (t, J=7.83 Hz, 1H) 7.87 (dd, J=9.22, 2.65 Hz, 1H) 7.97 (d, J=8.34 Hz, 1H) 8.26 (d, J=8.08 Hz, 1H) 8.29 (s, 1H) 10.52 (s, 1H) 13.10 (br. s., 1H).

Workup

  1. customazeotroped with toluene
  2. customtriturated in ether

Sources & evidence

ORD record
ord-d7b034bc0a7f488f9eb0a441e308a5cc
Source dataset
uspto-grants-2014_03
Patent number
US08680119B2

Reaction notes

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