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

HRID 3557

반응식

HRID 3557 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-44ee38b3384d451c8b68f82532c2510d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733905

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