Trifluoroacetic anhydride → HCID 22914615, compound

HRID 1378222Notes

Reaction equation

HRID 1378222 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:14][C:15]1[C:20]2[C:21](=[O:33])[N:22]([CH3:32])[CH2:23][C:24]3[N:25]([CH:26]=[N:27][C:28]=3[C:29]([NH2:31])=O)[C:19]=2[CH:18]=[CH:17][CH:16]=1>O1CCOCC1.N1C=CC=CC=1>[F:14][C:15]1[C:20]2[C:21](=[O:33])[N:22]([CH3:32])[CH2:23][C:24]3[N:25]([CH:26]=[N:27][C:28]=3[C:29]#[N:31])[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 22914609HCID 22914609, compound

Product 1

HCID 22914615HCID 22914615, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

7.7 ml (55.3 mmol) of trifluoroacetic anhydride were added dropwise at 5°-8° to a suspension of 13.8 g (50.3 mmol) of 7-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo-[1,5-a][1,4]benzodiazepine-3-carboxamide (EPA 150 040) in 80 ml of dioxan and 20 ml of pyridine. The beige solution obtained was stirred at 5° for 2.5 hours and subsequently poured into 220 ml of ice-water. The resulting precipitate was filtered off. After drying at 70°/10 Torr there were obtained 11 g (85%) of 7-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile as a white powder of m.p. >250°.

Workup

  1. customThe beige solution obtained
  2. filtrationThe resulting precipitate was filtered off
  3. customAfter drying at 70°/10 Torr there

Sources & evidence

ORD record
ord-400d66df95cf45c69c4d1b14c06f8503
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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