Trifluoroacetic acid → HCID 178436496, compound

HRID 1875161Notes

Reaction equation

HRID 1875161 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]#[CH:26])[CH:22]=[C:21]([Cl: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]=[C:23]([C:25]#[CH:26])[CH:22]=[C:21]([Cl:27])[CH:20]=2)[C:12]=1[F:28])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866449414-chloro-N-({4-chloro-3-[(3-chloro-5-ethynylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 178436496HCID 178436496, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-ethynylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (98.0 mg, 0.172 mmol) in DCM (5 ml) was added TFA (2.0 ml) and the reaction mixture was stirred at rt for 3 hours. The reaction was quenched with saturated sodium bicarbonate, diluted with EtOAc, 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-chloro-5-ethynylphenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (50.0 mg, 0.114 mmol, 66% yield) 1H NMR (400 MHz, DMSO-d6) δ ppm 8.09-8.30 (m, 1H), 7.73 (s, 1H), 7.45 (d, 1H), 7.22-7.36 (m, 2H), 7.08 (s, 1H), 6.88 (s, 1H), 4.49 (d, 2H), 4.37 (s, 1H). LC-MS (ES+) m/z 438.01, [M+H].

Workup

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

Sources & evidence

ORD record
ord-c4426e226ef341bd8b716ff401887f19
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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