Pyridine → HCID 54516569, compound

HRID 1378136Notes

Reaction equation

HRID 1378136 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.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[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 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 54132851HCID 54132851, compound

Product 1

HCID 54516569HCID 54516569, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

78 g (290 mmol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide were suspended in 380 ml of dioxan and 68 ml of pyridine and treated dropwise at 0° with 59 ml (424 mmol) of trifluoroacetic anhydride. After stirring at 50° for two hours the reaction mixture was poured into 2 l of ice-water and the crystals were filtered off under suction, rinsed with water and dried. 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 of m.p. 232°-234°.

Workup

  1. filtrationthe crystals were filtered off under suction
  2. washrinsed with water
  3. customdried

Sources & evidence

ORD record
ord-a06ef46278e045c9a245abd74feb9e4f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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