Trifluoroacetic acid → HCID 178436497, compound

HRID 1875153Notes

Reaction equation

HRID 1875153 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]([CH2:25][CH3:26])[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]([CH2:25][CH3:26])[CH:22]=[C:21]([Cl:27])[CH:20]=2)[C:12]=1[F:28])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684808764-chloro-N-({4-chloro-3-[(3-chloro-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 178436497HCID 178436497, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (64 mg, 0.112 mmol) in DCM (5 ml) was added TFA (2.0 ml) and the reaction mixture was stirred for 5 hours at room temperature. The reaction was quenched with saturated sodium bicarbonate 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-ethylphenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (28 mg, 0.063 mmol, 57% yield). 1H NMR (400 MHz, DMSO-d5) δ ppm 12.83-13.43 (m, 1H), 8.20 (d, 1H), 7.73 (s, 1H), 7.44 (d, 1H), 7.29 (t, 1H), 7.01 (s, 1H), 6.73 (s, 1H), 6.66 (s, 1H), 4.48 (d, 2H), 2.53 (q, 2H), 1.08 (t, 3H). LC-MS (ES+) m/z 441.59, [M+H].

Workup

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

Sources & evidence

ORD record
ord-d2a2f0007d64403b93d818c1700d87a0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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