Ammonia → N-(3-fluorophenyl)-N-(3,3,3-trifluoro-2-hydroxypropyl)-3-(trifluoromethyl)benzamide

HRID 1371098Notes

Reaction equation

HRID 1371098 reaction equation
FC(F)(F)C1C=C(C=CC=1)C([O:8][CH:9]([CH2:14][N:15]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)[C:16](=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:10]([F:13])([F:12])[F:11])=O.N>CO>[F:34][C:30]1[CH:29]=[C:28]([N:15]([CH2:14][CH:9]([OH:8])[C:10]([F:11])([F:12])[F:13])[C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 109519142,2,2-Trifluoro-1-[[(3-fluoro-phenyl)[3-(trifluoromethyl)benzoyl]amino]methyl]ethyl 3-trifluoromethyl-benzoate

Product 1

HCID 10949282N-(3-fluorophenyl)-N-(3,3,3-trifluoro-2-hydroxypropyl)-3-(trifluoromethyl)benzamideYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,2,2-trifluoro-1-[[(3-fluorophenyl)[3-(trifluoromethyl)benzoyl]amino]-methyl]ethyl 3-trifluoromethyl-benzoate (600 mg, 1.06 mmol) from EX-662 in methanol was treated with 28% ammonia solution (122 μL). The solution was stiffed at room temperature for 10 h. The reaction was quenched with water and extracted with ether. The ether layer was washed with brine and water, then dried over anhydrous MgSO4. The crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:8) to give 255 mg (61%) of the desired N-(3-fluorophenyl)-N-(3,3,3-trifluoro-2-hydroxypropyl)-3-(trifluoromethyl)benzamide product as a white (m 2H), 6.98 (m, 1H), 6.90 (m, 2H), 4.49 (dd, 1H), 4.34 (d, 1H), 4.26 (m, 1H), 4.01 (dd, 1H). 19F NMR (CDCl3) δ −64.7 (s, 3F), −80.3 (s, 3F), −111.0 (m, 1F). HRMS calcd. for C17H12F7NO2: 396.0854 [M+H]+, found: 396.0821.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. washThe ether layer was washed with brine and water
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:8)

Sources & evidence

ORD record
ord-a015ebea33e8405fa628899016dfee8d
Source dataset
uspto-grants-2003_06
Patent number
US06583183B2

Reaction notes

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