Trifluoroacetic acid → HCID 11645798, compound

HRID 1644857Notes

Reaction equation

HRID 1644857 reaction equation
FC(F)(F)C(O)=O.[N:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[C:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:22][C:21]=3[C:29]([NH:31]C(C)(C)C)=[O:30])=[CH:16][CH:15]=2)[CH:12]=[CH:11][N:10]=[CH:9]1>C1(OC)C=CC=CC=1>[N:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[C:23]([CH2:25][CH:26]([CH3:27])[CH3:28])[S:22][C:21]=3[C:29]([NH2:31])=[O:30])=[CH:16][CH:15]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11574777HCID 11574777, compound

Product 1

HCID 11645798HCID 11645798, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

Trifluoroacetic acid was added (2.5 mL) to 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene,2-carboxamide (165 mg, 0.417 mmol, see step (d) above), and one drop (ca. 0.05 mL) of anisol was added to the reaction mixture. The mixture was stirred under a N2 atmosphere for 30 hours and then evaporated and co-evaporated with acetonitrile. The crude product was purified by column chromatography (CH2Cl2:MeOH (85:15)) to give the sub-title compound (117 mg, 0.345 mmol) in 73% yield.

Workup

  1. additionwas added to the reaction mixture
  2. customevaporated
  3. customThe crude product was purified by column chromatography (CH2Cl2:MeOH (85:15))

Sources & evidence

ORD record
ord-a5ca1e1c368c401ab4c0f055c82ad33e
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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