Cesium carbonate → 4(Indol-6-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline

HRID 454096

반응식

HRID 454096 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[CH:30][NH:31]2)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[NH:31]1[C:32]2[C:28](=[CH:27][CH:26]=[C:25]([O:24][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:33]=2)[CH:29]=[CH:30]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 5245086-HydroxyindoleHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazoline

생성물 1

HCID 220309204(Indol-6-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A solution of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (200 mg, 0.59 mmol), (prepared as described for the starting material in Example 67), 6-hydroxyindole (96 mg, 0.715 mmol) in DMF (3 ml) containing cesium carbonate (291 mg, 0.894 mmol) was heated at 90° C. for 4 hours. After cooling, the mixture was diluted with water, the precipitate was filtered, washed with water and dried under vacuum. The solid was purified by column chromatography eluting with methylene chloride/methanol (90/10 increasing to 50/50) to give 4-(indol-6-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline (240 mg, 93%).

후처리

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. customThe solid was purified by column chromatography
  6. washeluting with methylene chloride/methanol (90/10 increasing to 50/50)

출처 및 근거

ORD 기록
ord-bb8fb3b170d44f6bbaadb6e5483d0bba
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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