Methanol → 5,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

HRID 3557

Reaction equation

HRID 3557 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9](=O)[CH2:10][C:4]2=[N:3][N:2]=1.B.CSC.CO>O1CCCC1>[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][CH2:9][CH2:10][C:4]2=[N:3][N:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 218371285,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one

Product 1

HCID 218370045,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 7.0 g of 5,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one in 25 ml of tetrahydrofuran is added 9 ml of 10M borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours, cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum and to the residue is added 100 ml of 2N sodium hydroxide. The mixture is refluxed for 5 hours, chilled and extracted with dichloromethane. The extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed under vacuum to give a solid. The solid is purified by chromatography on silica gel to give the desired product.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customThe volatiles are removed under vacuum and to the residue
  3. additionis added 100 ml of 2N sodium hydroxide
  4. temperatureThe mixture is refluxed for 5 hours
  5. temperaturechilled
  6. extractionextracted with dichloromethane
  7. washThe extract is washed with 2N citric acid, water
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed under vacuum
  10. customto give a solid
  11. customThe solid is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-44ee38b3384d451c8b68f82532c2510d
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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