Acetic Acid → 1-[(10-Chloro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-yl)carbonyl]-3-methoxyazetidine

HRID 1885355노트

반응식

HRID 1885355 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#N)[C:3]=1[C:10]1[NH:11][C:12](=[O:30])[C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:14][C:15]=1[C:16]([N:18]1[CH2:21][CH:20]([O:22][CH3:23])[CH2:19]1)=[O:17].C(O)(=O)C>[Zn].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:10]1=[C:15]([C:16]([N:18]3[CH2:21][CH:20]([O:22][CH3:23])[CH2:19]3)=[O:17])[CH:14]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:12](=[O:30])[N:11]1[CH2:8]2

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 197854571-[[2-(2-Chloro-6-cyanophenyl)-1,6-dihydro-6-oxo-5-phenyl-3-pyridyl]carbonyl]-3-methoxyazetidine

생성물 1

HCID 189570571-[(10-Chloro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-yl)carbonyl]-3-methoxyazetidine수율 29.1%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 962Water용매

실험 절차

A mixture of 1.17 g of 1-[[2-(2-chloro-6-cyanophenyl)-1,6-dihydro-6-oxo-5-phenyl-3-pyridyl]carbonyl]-3-methoxyazetidine, 0.91 g of zinc powder and 25 ml of acetic acid was heated to boiling under reflux for 15 minutes under argon. The reaction mixture was then poured into 125 ml of water, whereupon the separated crystals were filtered off under suction and washed with water. The aqueous phase was exhaustively extracted with methylene chloride. The combined organic phases were evaporated and the residue was purified with the crystals obtained above. This material was chromatographed on silica gel with methylene chloride/acetone (9:1) and then recrystallized from toluene. There was obtained 0.33 g of 1-[(10-chloro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindol-1-yl)carbonyl]-3-methoxyazetidine as yellow crystals with a m.p. of 235°-238°.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 15 minutes under argon
  3. filtrationwere filtered off under suction
  4. washwashed with water
  5. extractionThe aqueous phase was exhaustively extracted with methylene chloride
  6. customThe combined organic phases were evaporated
  7. customthe residue was purified with the crystals
  8. customobtained above
  9. customThis material was chromatographed on silica gel with methylene chloride/acetone (9:1)
  10. customrecrystallized from toluene

출처 및 근거

ORD 기록
ord-b29f5917d04a4476bacea58498b2c614
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05143912

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