Dichloromethane → 5,11-Dihydro-11-ethyl-6-methanesulfonyloxy-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine

HRID 53537

반응식

HRID 53537 반응식
F[C:2](F)(F)[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16]([N:18]1[C:24]2[N:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:22](=O)[NH:21][C:20]2[C:30]([CH3:35])=[CH:31][C:32]([CH3:34])=[N:33][C:19]1=2)[CH3:17].C(Cl)Cl.C(N(C(C)C)CC)(C)C>[C-]#N.C([N+](CC)(CC)CC)C.C(OCC)(=O)C>[CH2:16]([N:18]1[C:24]2[N:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:22]([O:6][S:3]([CH3:2])(=[O:5])=[O:4])[NH:21][C:20]2[C:30]([CH3:35])=[CH:31][C:32]([CH3:34])=[N:33][C:19]1=2)[CH3:17]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 463543Dipyridodiazepinone deriv. 5

생성물 1

HCID 199600595,11-Dihydro-11-ethyl-6-methanesulfonyloxy-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine수율 7.9%

시약·촉매·용매 2

HCID 3014735Tetraethylammonium cyanide촉매HCID 8857Ethyl Acetate용매

실험 절차

Trifluoromethanesulfonic anhydride (0.24 ml, 14 mmol) was added to a solution of 0.314 g (1.2 mmol) 5,11-dihydro-11-ethyl-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one in 15 ml of methylene chloride containing 0.25 ml (14 mmol) of diisopropylethylamine, and the resulting mixture was refluxed under argon for three hours. Ethyl acetate (~200 mL) was then added and the solution was washed three times with water and four times with brine. After drying (magnesium sulfate), the solution was concentrated in vacuo and the residue dried under high vacuum for 2 hr. The residue was dissolved in 20 ml of methylene chloride, and 0.23 g (14 mol) of tetraethylammonium cyanide was added. After stirring the resulting solution overnight at room temperature, the reaction mixture was concentrated in vacuo. The residue was dissolved in 100 ml of ethyl acetate, and the solution was washed with water and brine. The dried (magnesium sulfate) solution was concentrated in vacuo and the residue was chromatographed over silica with 5% ethyl acetate/hexane. The resulting solid was crystallized from heptane to provide 0.033 g of the title compound as red crystals, m.p. 154°-155° C.

후처리

  1. temperaturethe resulting mixture was refluxed under argon for three hours
  2. washthe solution was washed three times with water and four times with brine
  3. dry with materialAfter drying (magnesium sulfate)
  4. concentrationthe solution was concentrated in vacuo
  5. customthe residue dried under high vacuum for 2 hr
  6. dissolutionThe residue was dissolved in 20 ml of methylene chloride
  7. concentrationthe reaction mixture was concentrated in vacuo
  8. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  9. washthe solution was washed with water and brine
  10. dry with materialThe dried (magnesium sulfate) solution
  11. concentrationwas concentrated in vacuo
  12. customthe residue was chromatographed over silica with 5% ethyl acetate/hexane
  13. customThe resulting solid was crystallized from heptane

출처 및 근거

ORD 기록
ord-98afc215bffc439da9f9d0bb71a57fb3
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620974

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