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

HRID 1418959Notes

Reaction equation

HRID 1418959 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].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>O1CCOCC1.N1C=CC=CC=1>[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 3

HCID 8857Ethyl AcetateHCID 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 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 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]benzodiazepin-3-carboxamide in a mixture of 60 ml of dioxan and 8 ml of pyridine was treated dropwise at 0° with 6.8 ml (0.049 mol) of trifluoroacetic anhydride. The dark solution was stirred at 50° for 3 hrs., cooled, poured on to 400 ml of icewater, treated with ethyl acetate and extracted. The organic solution was filtered on 100 g of silica gel and rinsed with 200 ml of ethyl acetate. The product was recrystallized from m hot ethyl acetate. 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. temperature, cooled
  2. additionpoured on to 400 ml of icewater
  3. extractionextracted
  4. filtrationThe organic solution was filtered on 100 g of silica gel
  5. washrinsed with 200 ml of ethyl acetate
  6. customThe product was recrystallized from m hot ethyl acetate

Sources & evidence

ORD record
ord-2cb50fa6f01648968c02600b0819666d
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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