Trifluoroacetic anhydride → HCID 54516569, compound

HRID 1418933Notes

Reaction equation

HRID 1418933 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([NH2:18])=O)=[C:5]2[C@@H:4]2[CH2:19][CH2:20][N:3]12.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.N1C=CC=CC=1>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]#[N:18])=[C:5]2[C@@H:4]2[CH2:19][CH2:20][N:3]12

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 54132851HCID 54132851, compound

Product 1

HCID 54516569HCID 54516569, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 78 g (0.78 g mol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide in a mixture of 380 ml of dioxan and 68 ml of pyridine was treated dropwise at 0° with 59 ml (0.424 mol) of trifluoroacetic anhydride. The suspension was stirred at 50° for 2 hrs., cooled and poured on to 2 l of ice-water. After vigorous stirring the suspension was suction filtered. There were obtained 60 g (82%) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile; m.p. 232°-234°.

Workup

  1. temperature, cooled
  2. stirringAfter vigorous stirring the suspension
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9f1ab613a8874e6daf0b839c5e570e42
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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