8-bromo-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine → 1-(dimethylamino)methyl-8-bromo-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 1414358Notes

Reaction equation

HRID 1414358 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:6]=2[CH:21]=1>CN(C)C=O>[CH3:10][N:11]([CH2:12][C:12]1[N:11]2[C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:21][C:6]=3[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:8][CH2:9][C:10]2=[N:14][N:13]=1)[CH3:5]

Participants

3

Reactant 1

HCID 125625168-bromo-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 126123801-(dimethylamino)methyl-8-bromo-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of this reagent in 10 ml. of dimethylformamide was added 3.00 mmol of 8-bromo-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine. The mixture was heated to 80° for a total of 24 hours, then quenched in cold water, neutralized with a 10% aqueous sodium hydroxide solution and extracted with chloroform. The chloroform layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil, which was chromatographed over 100 g. of silica gel by eluting with 3% methanol/97% chloroform mixtures. The product was collected and crystallized from ethyl acetate to yield 1-(dimethylamino)methyl-8-bromo-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine of melting point 163.5°- 165° C.

Workup

  1. additionTo a suspension of this reagent in 10 ml
  2. temperatureThe mixture was heated to 80° for a total of 24 hours
  3. customquenched in cold water
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo to an oil, which
  8. customwas chromatographed over 100 g
  9. washof silica gel by eluting with 3% methanol/97% chloroform
  10. customThe product was collected
  11. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-849680a7bc7e441c94eddf29fa16d1b4
Source dataset
uspto-grants-1977_01
Patent number
US04001262

Reaction notes

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