Potassium Carbonate → 7-(3-(1,1-Dioxothiomorpholino)propoxy)-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline

HRID 1791789노트

반응식

HRID 1791789 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][CH:17]=[C:16]4[CH3:22])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:23][CH3:24].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(OO[CH2:36][CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][S:42](=[O:46])(=[O:45])[CH2:41][CH2:40]1)(=O)=O>CN(C=O)C>[O:46]=[S:42]1(=[O:45])[CH2:43][CH2:44][N:39]([CH2:38][CH2:37][CH2:36][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([O:12][C:13]4[CH:14]=[C:15]5[C:19](=[CH:20][CH:21]=4)[NH:18][CH:17]=[C:16]5[CH3:22])=[N:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:23][CH3:24])[CH2:40][CH2:41]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 876873553-(1,1-Dioxothiomorphlino)propoxy tosylateHCID 1357631157-Hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline

생성물 1

HCID 220306597-(3-(1,1-Dioxothiomorpholino)propoxy)-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline수율 56.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

A mixture of 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (600 mg, 1.87 mmol), (prepared as described for the starting material in Example 271), potassium carbonate (773 mg, 5.60 mmol) and 3-(1,1-dioxothiomorphlino)propoxy tosylate (1.296 g, 3.74 mmol) in DMF (30 ml) was stirred at 75° C. overnight and allowed to cool to ambient temperature. The reaction mixture was filtered and the solvent removed in vacuo. The residue was purified by silica column chromatography, gradient elution (dichloromethane, 5% methanol/95% dichloromethane, methanol/dichloromethane/0.880 saturated aqueous ammonia (100/8/1)) and the product recrystallised from ethanol to give 7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (525 mg, 56%).

후처리

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by silica column chromatography, gradient elution (dichloromethane, 5% methanol/95% dichloromethane, methanol/dichloromethane/0.880 saturated aqueous ammonia (100/8/1))
  6. customthe product recrystallised from ethanol

출처 및 근거

ORD 기록
ord-233237a2c74449d28a2d406ee16b0bd3
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074800B1

반응 노트

불러오는 중…