Ammonia → 8-chloro-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine-2-carboxamide

HRID 66231Notes

Reaction equation

HRID 66231 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([C:15]([O:17]C)=O)[CH:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]=2[CH:25]=1.[NH3:26]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([C:15]([NH2:26])=[O:17])[CH:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 123778848-Chloro-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid, methyl ester

Product 1

HCID 123778878-chloro-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 750 mg. (2.13 mmol) of the end product of Example 9 in 50 ml. methanol in a glass bomb was cooled to 3° and saturated with ammonia. The glass bomb was then sealed and the reaction heated to 70° with stirring, for 16 hours. After cooling to 5°, the bomb was opened, the contents transferred to a r.b. flask and concentrated in vacuo. Recrystallization was acetone/hexane yielded end product, mp 216°-218°. An analytical sample was prepared by an additional recrystallization from acetone/hexane and obtained as pale yellow needles: mp 217°-219°.

Workup

  1. customThe glass bomb was then sealed
  2. temperaturethe reaction heated to 70°
  3. temperatureAfter cooling to 5°
  4. concentrationflask and concentrated in vacuo
  5. customRecrystallization
  6. customAn analytical sample was prepared by an additional recrystallization from acetone/hexane
  7. customobtained as pale yellow needles

Sources & evidence

ORD record
ord-0523aa3b6d334cb395c93f567a2e720b
Source dataset
uspto-grants-1978_12
Patent number
US04130716

Reaction notes

Loading…