Acetohydrazide → 4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

HRID 1485438Notes

Reaction equation

HRID 1485438 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH:9](C)[C:8](=S)[NH:7][C:6]=2[CH:14]=1.[C:15]([NH:18][NH2:19])(=O)C>C(O)CCC>[CH:15]1[N:7]2[C:6]3[CH:14]=[CH:2][CH:3]=[CH:4][C:5]=3[N:11]=[CH:10][CH2:9][C:8]2=[N:19][N:18]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 867185058-fluoro-3-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione

Product 1

HCID 867185014H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 8-fluoro-3-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione (5.0 g, 23.8 mmol) and acetohydrazide (2.64 g, 35.7 mmol) in n-butanol (60 mL) was heated at 130° C. for 15 hours. The mixture was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1-2:1) to afford 4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine, 5,6-dihydro-1,4-dimethyl-9-fluoro-as an off-white solid (1.9 g, 34%). LRMS (M+H)+: calcd 232.11. found 232.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1-2:1)

Sources & evidence

ORD record
ord-45c0007a9df749abbc3bc0f55ad85b8b
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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