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

HRID 256693노트

반응식

HRID 256693 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 2%

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]isoindole-1-yl)carbonyl]-3-methoxyazetidine as yellow crystals with a m.p. of 235°-238°.

후처리

  1. additionA mixture of 1
  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-bde840441c1a4b9ea74bae8b11033ed2
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258387

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