Water → 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

HRID 1378211Notes

Reaction equation

HRID 1378211 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:18])=O)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:21].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>O1CCOCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:18])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 218422317-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-carboxamide

Product 1

HCID 218422677-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

14.4 g (0.0466 mol) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide was suspended in 60 ml of dioxan and 8 ml of pyridine and treated dropwise at a temperature of ~8° within 10 min. with 10.3 g (0.049 mol) of trifluoroacetic anhydride. The mixture was stirred at 50° for 3 hours and poured into 400 ml of water. The mixture was extracted with ethyl acetate, dried over magnesium sulfate, filtered and the filtrate was concentrated. The residue was dissolved in 300 ml of hot ethyl acetate, the solution was suction filtered over 100 g of silica gel, the silica gel was rinsed with 200 ml of ethyl acetate and the filtrate was evaporated. There were obtained 12 g (89%) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile as light yellowish crystals; m.p. 221°-223°.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in 300 ml of hot ethyl acetate
  6. filtrationfiltered over 100 g of silica gel
  7. washthe silica gel was rinsed with 200 ml of ethyl acetate
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-718c0ae9c4f54b808e0775a624029e7c
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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