Potassium Carbonate → 3-Cyano-6-methoxy-4-(2,3-methylenedioxyphenoxy)-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline

HRID 1784101

반응식

HRID 1784101 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[O:15][C:14]2[C:9](=[C:10]([OH:16])[CH:11]=[CH:12][CH:13]=2)[O:8]1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][C:19]=1[C:41]#[N:42]>CN(C=O)C>[C:41]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:18]=1[O:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]3[O:15][CH2:7][O:8][C:9]=13)=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][CH2:32][CH2:33][N:34]1[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]1)[CH:23]=2)#[N:42]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5867271,3-Benzodioxol-4-olHCID 117491774-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile

생성물 1

HCID 179805913-Cyano-6-methoxy-4-(2,3-methylenedioxyphenoxy)-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline수율 54.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Potassium carbonate-(0.055 g) was added to a solution of 2,3-methylenedioxyphenol (0.041 g) in DMF (3 ml) and the mixture was stirred at ambient temperature for 10 minutes. 4-Chloro-3-cyano-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline (0.1 g) was added and the mixture was stirred and heated to 95° C. for 2 hours. The resultant mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was purified by colum chromatography on silica using initially increasingly polar mixtures of methylene chloride and methanol followed by increasingly polar mixtures of methylene chloride and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.069 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 2.3-2.4 (m, 2H), 3.0 (s, 3H), 3.2-4.0 (m, 8H), 3.5 (m, 2H), 3.95 (s, 3H), 4.4 (m, 2H), 6.05 (s, 2H), 6.8 (m, 1H), 6.9 (m, 2H), 7.6 (s, 1H), 7.62 (s, 1H), 9.1 (s, 1H); Mass Spectrum: M+H+ 477.

후처리

  1. stirringthe mixture was stirred
  2. temperatureheated to 95° C. for 2 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was purified by colum chromatography on silica using initially increasingly polar mixtures of methylene chloride and methanol
  6. temperatureby increasingly polar mixtures of methylene chloride

출처 및 근거

ORD 기록
ord-a5d66199e62444b397bafa9b4178fe74
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501516B2

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