Hydrochloric Acid → 6-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one

HRID 1791692노트

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HRID 1791692 반응식
ClC1C=CC([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]4)=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=C(F)C=1.Cl.C(=O)([O-])O.[Na+]>>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)[N:10]=[CH:9][NH:8][C:7]2=[O:6]

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 218748154-(4-Chloro-2-fluorophenoxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

생성물 1

HCID 1354581696-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one수율 96.7%

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온도
95 °C

실험 절차

4-(4-Chloro-2-fluorophenoxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (2.6 g, 5.6 mmol) was treated with 2.0 N aqueous hydrochloric acid (45 ml) and the mixture stirred at 95° C. for 2 hours. The mixture was cooled, basified by the addition of solid sodium hydrogen carbonate and the water removed by azeotroping with toluene. The residue was purified by silica column chromatography eluting with dichloromethane/methanol/0.880 aqueous ammonia (50/8/1) to give 6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one (1.8 g, 96%).

후처리

  1. temperatureThe mixture was cooled
  2. customthe water removed
  3. customby azeotroping with toluene
  4. customThe residue was purified by silica column chromatography
  5. washeluting with dichloromethane/methanol/0.880 aqueous ammonia (50/8/1)

출처 및 근거

ORD 기록
ord-ce966b7d00e34720838fdfe6a72f7ac8
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074800B1

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