Trifluoroacetic acid → HCID 178522959, compound

HRID 1875149Notes

Reaction equation

HRID 1875149 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:35])=[C:12]([CH2:17][NH:18][C:19]([C:21]3[N:25](COCC[Si](C)(C)C)[CH:24]=[N:23][C:22]=3[Cl:34])=[O:20])[CH:13]=[CH:14][C:15]=2[Cl:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:35])=[C:12]([CH2:17][NH:18][C:19]([C:21]3[NH:25][CH:24]=[N:23][C:22]=3[Cl:34])=[O:20])[CH:13]=[CH:14][C:15]=2[Cl:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68487164N-({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 178522959HCID 178522959, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (120 mg, 0.192 mmol) in DCM (5 ml) was added TFA (1.0 mL) and the mixture was stirred at room temperature for 3 hours. The solvent was removed and the crude material was purified via reverse phase HPLC to give N-({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (78 mg, 0.158 mmol, 82% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.12 (d, 1H), 8.02-8.42 (m, 1H), 7.73 (s, 1H), 7.41-7.54 (m, 1H), 7.32 (t, 1H), 7.08-7.15 (m, 1H), 6.95-7.06 (m, 1H), 4.49 (d, 2H). LC-MS (ES+) m/z 491.87, [M+H].

Workup

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

Sources & evidence

ORD record
ord-373ff35f216843db90270c9642e54118
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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