Vesnarinone → 1-(2-Propynyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649237

반응식

HRID 1649237 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)[CH2:10][CH2:9]1)=[O:7].[H-].[Na+].[CH2:32](Cl)[C:33]#[CH:34]>CN(C=O)C>[CH2:34]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:13][CH2:12]3)=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]1=[O:24])[C:33]#[CH:32]

참가 물질

5

반응물 3

HCID 5663VesnarinoneHCID 122213-Chloro-1-propyneHCID 24758Sodium hydride

생성물 1

HCID 132363951-(2-Propynyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril수율 15.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (1.96 g) and 0.25 g of 50% oily sodium hydride were mixed with 60 ml of DMF and stirred at room temperature for 2 hours. Then, to the mixture was added 0.66 g of propargyl chloride and the mixture was stirred at room temperature for 7 hours. The reaction mixture was poured into a 150 ml of saturated saline solution and organic substances were extracted with chloroform. The chloroform layer was washed with water and dehydrated. Chloroform was distilled off and the residue was purified through silica gel column chromatography followed by recrystallization from ethanol to give 0.34 g of 1-(2-propynyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 152°-154° C., pale yellow needles.

후처리

  1. stirringthe mixture was stirred at room temperature for 7 hours
  2. extractionwere extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. distillationChloroform was distilled off
  5. customthe residue was purified through silica gel column chromatography
  6. customfollowed by recrystallization from ethanol

출처 및 근거

ORD 기록
ord-86825a66dd2a46d7b1723ebedb9e44e3
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04415572

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