Trifluoroacetic acid → HCID 178522957, compound

HRID 1875200Notes

Reaction equation

HRID 1875200 reaction equation
[Br:1][C:2]1[C:3]([F:38])=[CH:4][C:5]([N+:35]([O-:37])=[O:36])=[C:6]([O:8][C:9]2[C:10]([F:34])=[C:11]([CH2:16][NH:17][C:18]([C:20]3[N:24](COCC[Si](C)(C)C)[CH:23]=[N:22][C:21]=3[Cl:33])=[O:19])[CH:12]=[CH:13][C:14]=2[Cl:15])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([F:38])=[CH:4][C:5]([N+:35]([O-:37])=[O:36])=[C:6]([O:8][C:9]2[C:10]([F:34])=[C:11]([CH2:16][NH:17][C:18]([C:20]3[NH:24][CH:23]=[N:22][C:21]=3[Cl:33])=[O:19])[CH:12]=[CH:13][C:14]=2[Cl:15])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68486195N-({3-[(5-bromo-4-fluoro-2-nitrophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 178522957HCID 178522957, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-({3-[(5-bromo-4-fluoro-2-nitrophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5carboxamide (55.0 mg, 0.084 mmol) in DCM (6 ml) was added TFA (3.00 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 N-({3-[(5-bromo-4-fluoro-2-nitrophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (33 mg, 0.063 mmol, 75% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.03 (d, 1H), 7.74 (s, 1H), 7.32-7.45 (m, 2H), 7.10 (d, 1H), 4.65 (s, 2 H). LC-MS (ES+) m/z 520.92, [M+H].

Workup

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

Sources & evidence

ORD record
ord-95850d5ba6df4158a3ff8111d98840e2
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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