Trifluoroacetic acid → HCID 178510238, compound

HRID 1875205Notes

Reaction equation

HRID 1875205 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]=[CH:23][C:22]([F:25])=[C:21]([C:26]#[N:27])[CH:20]=2)[C:12]=1[F:28])=[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]=[CH:23][C:22]([F:25])=[C:21]([C:26]#[N:27])[CH:20]=2)[C:12]=1[F:28])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68721995HCID 68721995, compound

Product 1

HCID 178510238HCID 178510238, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-({4-chloro-3-[(3-cyano-4-fluorophenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (45 mg, 0.081 mmol) in DCM (4 ml) was added TFA (2.0 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-4-fluorophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (19 mg, 0.045 mmol, 55% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.74 (s, 1H) 7.29-7.40 (m, 3H) 7.13-7.29 (m, 2H) 4.61 (s, 2H). LC-MS (ES+) m/z 423.12, [M+H].

Workup

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

Sources & evidence

ORD record
ord-1be138b0e61d4b6bacd493a2910de5da
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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