Trifluoroacetic acid → HCID 178510241, compound

HRID 1875163Notes

Reaction equation

HRID 1875163 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]#[N:30])[CH:20]=2)[C:12]=1[F:31])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[C:21]([C:29]#[N:30])[CH:20]=2)[C:12]=1[F:31])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866449424-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 178510241HCID 178510241, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (97 mg, 0.161 mmol) in DCM (7 ml) was added TFA (3 ml) and the reaction mixture was stirred at rt for 2 hours. The reaction mixture was quenched with saturated sodium bicarbonate and the organic layer was separated. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (45 mg, 0.095 mmol, 59% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.82 (s, 1H), 7.69 (s, 1H), 7.47-7.53 (m, 2H), 7.35-7.42 (m, 2H), 4.63 (s, 2H). LC-MS (ES+) m/z 473.07, [M+H].

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate
  2. customthe organic layer was separated
  3. customThe solvent was removed
  4. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-3bdcb7e4e392469ab161182349e31e2d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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