Methylhydrazine → (S)-8-chloro-1-(1,3-dimethyl-1H-1,2,4-triazol-5-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

HRID 867533Notes

Reaction equation

HRID 867533 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:27])[N:9]3[CH2:26][CH2:25][CH2:24][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:18]=[C:19](N(C)C)[CH3:20])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:28][NH:29][NH2:30]>C(O)(=O)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:27])[N:9]3[CH2:26][CH2:25][CH2:24][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:29]([CH3:28])[N:30]=[C:19]([CH3:20])[N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 54118268(S)-8-chloro-N-[1-(dimethylamino)ethylidene]-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

Product 1

HCID 53750533(S)-8-chloro-1-(1,3-dimethyl-1H-1,2,4-triazol-5-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.96 g (10.3 mmol) of (S)-8-chloro-N-[1-(dimethylamino)ethylidene]-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide, 25 ml of glacial acetic acid and 0.65 ml (12.4 mmol) of methylhydrazine is stirred at 90° for 1.75 hours. The solution is then evaporated in vacuo and the residue is chromatographed on silica gel while eluting with ethyl acetate/methanol (19:1). After recrystallization from methylene chloride/ethyl acetate there is obtained (S)-8-chloro-1-(1,3-dimethyl-1H-1,2,4-triazol-5-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 221°-222°.

Workup

  1. customThe solution is then evaporated in vacuo
  2. customthe residue is chromatographed on silica gel
  3. washwhile eluting with ethyl acetate/methanol (19:1)
  4. customAfter recrystallization from methylene chloride/ethyl acetate there

Sources & evidence

ORD record
ord-00ca1543cf3e4bfcb05a3e82ae775ccd
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

Loading…