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Potassium Carbonate → HCID 53976813, 화합물

HRID 454290
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HRID 454290 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]=[CH:16]4)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:41][C@@H:42]2[O:44][CH2:43]2)(=O)=O)=CC=1>CC(N(C)C)=O>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][C:6]3[C:5]4[C:10](=[CH:11][C:2]([O:1][CH2:41][C@H:42]5[CH2:43][O:44]5)=[C:3]([O:22][CH3:23])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:21][CH:20]=2)[CH:16]=[CH:17]1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 1357631167-hydroxy-4-(1H-indol-5-yloxy)-6-methoxyquinazoline

생성물 1

HCID 53976813HCID 53976813, 화합물수율 53%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
60 °C

실험 절차

Nitrogen was bubbled through a mixture of 7-hydroxy-4-(indol-5-yloxy)-6-methoxyquinazoline (3.07 g, 10 mmol), (prepared as described for the starting material in Example 107), potassium carbonate (4.14 g, 30 mmol) and (2R)-(−)-glycidyl tosylate (4.57 g, 20 mmol) in DMA (35 ml) for 5 minutes. The mixture was then stirred at 60° C. for 2 hours under an atmosphere of nitrogen and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica by gradient elution with dichloromethane/methanol (100/0 to 95/5), to give (2R)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline as a yellow solid (1.92 g, 53%).

후처리

  1. custom(prepared
  2. customfor 5 minutes
  3. temperatureto cool to ambient temperature
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica by gradient elution with dichloromethane/methanol (100/0 to 95/5)

출처 및 근거

ORD 기록
ord-8cdc97e2f0014ff89f75835a9d8bd8e1
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492560B2

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