Trifluoroacetic acid → HCID 178440984, compound

HRID 1875166Notes

Reaction equation

HRID 1875166 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([O:12][C:13]2[C:14]([F:38])=[C:15]([CH2:20][NH:21][C:22]([C:24]3[N:28](COCC[Si](C)(C)C)[CH:27]=[N:26][C:25]=3[Cl:37])=[O:23])[CH:16]=[CH:17][C:18]=2[Cl:19])[CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH2:1]([C:5]1[CH:6]=[C:7]([O:12][C:13]2[C:14]([F:38])=[C:15]([CH2:20][NH:21][C:22]([C:24]3[NH:28][CH:27]=[N:26][C:25]=3[Cl:37])=[O:23])[CH:16]=[CH:17][C:18]=2[Cl:19])[CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68483744N-({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 178440984HCID 178440984, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (148 mg, 0.246 mmol) in DCM (5 ml) was added TFA (3.0 ml) and the reaction mixture was stirred at rt for 2 hours. The reaction mixture was neutralized with saturated sodium bicarbonate, diluted with EtOAc, and the organic layer was separated. The solvent was evaporated and the crude material was purified via silica gel chromatography to give N-({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (94 mg, 0.200 mmol, 81% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.69 (s, 1H), 7.24-7.37 (m, 2H), 6.90 (s, 1H), 6.56-6.66 (m, 2H), 4.62 (s, 2H), 2.53 (t, 2H), 1.51 (qd, 2H), 1.20-1.35 (m, 2H), 0.88 (t, 3H). LC-MS (ES+) m/z 469.93, [M+H].

Workup

  1. customthe organic layer was separated
  2. customThe solvent was evaporated
  3. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-fd892e67454148d0898e914212cf0bda
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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