Acetic Anhydride → HCID 178506310, compound

HRID 216404Notes

Reaction equation

HRID 216404 reaction equation
[F:1][C:2]([F:31])([F:30])[C@@:3]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)=[CH:21][CH:20]=1)(O)[CH2:4][C:5]1[NH:6][CH:7]=[C:8]([CH2:10][C:11]2([C:14]([F:17])([F:16])[F:15])[CH2:13][CH2:12]2)[N:9]=1.C(OC(=O)C)(=O)C.[OH-].[Na+]>C(O)(=O)C>[F:31][C:2]([F:1])([F:30])/[C:3](/[C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)=[CH:23][CH:24]=1)=[CH:4]\[C:5]1[NH:6][CH:7]=[C:8]([CH2:10][C:11]2([C:14]([F:15])([F:16])[F:17])[CH2:12][CH2:13]2)[N:9]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 178520388HCID 178520388, compound

Product 1

HCID 178506310HCID 178506310, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of (2R)-1,1,1-trifluoro-2-[4-(1H-pyrazol-1-yl)phenyl]-3-(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1H-imidazol-2-yl)propan-2-ol in acetic acid (10 mL)/acetic anhydride (10 mL) was heated to reflux. The reaction mixture was poured into 1M sodium hydroxide solution until basic and extracted with diethyl ether. The crude product was dissolved in a mixture of methanol and acetonitrile and charged with 1M sodium hydroxide. It was heated to reflux overnight, and the reaction mixture was extracted with diethyl ether. The combined organic extracts were washed with brine, dried (potassium carbonate) and concentrated in vacuo to afford 1-{4-[(Z)-1-(trifluoromethyl)-2-(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1H-imidazol-2-yl)vinyl]phenyl}-1H-pyrazole, which was used without further purification.

Workup

  1. temperaturewas heated to reflux
  2. extractionextracted with diethyl ether
  3. dissolutionThe crude product was dissolved in a mixture of methanol and acetonitrile
  4. additioncharged with 1M sodium hydroxide
  5. temperatureIt was heated
  6. temperatureto reflux overnight
  7. extractionthe reaction mixture was extracted with diethyl ether
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (potassium carbonate)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-025df225d1694e3580d3d9118408d1a6
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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