Trifluoroacetic acid → HCID 178510240, compound

HRID 1875186Notes

Reaction equation

HRID 1875186 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]([CH:25]([F:27])[F:26])[CH:22]=[C:21]([C:28]#[N:29])[CH:20]=2)[C:12]=1[F:30])=[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]([CH:25]([F:26])[F:27])[CH:22]=[C:21]([C:28]#[N:29])[CH:20]=2)[C:12]=1[F:30])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68488028HCID 68488028, compound

Product 1

HCID 178510240HCID 178510240, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(difluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (81 mg, 0.138 mmol) dissolved in DCM (5 ml) was added TFA (2.00 ml) and the reaction mixture was stirred at RT for 2 hours. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(difluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (56 mg, 0.123 mmol, 89% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.77 (s, 1H), 7.65 (s, 1H), 7.23-7.50 (m, 4H), 6.81 (t, 1H), 4.64 (s, 2H). LC-MS (ES+) m/z 454.97, [M+H].

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-f9702465bddb45efa4ea86696234cf0f
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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