Potassium Carbonate → (RS)-N-(Ethoxycarbonyl)-S-ethyl-S-[3-({[4-(isopropylamino)-6-methoxy-quinazolin-7-yl]oxy}methyl)phenyl]sulphoximide

HRID 249978노트

반응식

HRID 249978 반응식
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].Br[CH2:19][C:20]1[CH:21]=[C:22]([S:26]([CH2:34][CH3:35])(=[N:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:27])[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:32]([O:31][C:29]([N:28]=[S:26]([CH2:34][CH3:35])([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][O:17][C:11]2[CH:10]=[C:9]3[C:14]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][CH:7]=[N:8]3)=[CH:13][C:12]=2[O:15][CH3:16])[CH:21]=1)=[O:27])=[O:30])[CH3:33]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 57787996(RS)-S-[3-(bromomethyl)phenyl]-N-(ethoxycarbonyl)-S-ethylsulphoximideHCID 1358608004-(Isopropylamino)-6-methoxyquinazolin-7-ol

생성물 1

HCID 57788042(RS)-N-(Ethoxycarbonyl)-S-ethyl-S-[3-({[4-(isopropylamino)-6-methoxy-quinazolin-7-yl]oxy}methyl)phenyl]sulphoximide수율 62%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

4-(Isopropylamino)-6-methoxyquinazolin-7-ol (50 mg, 0.21 mmol) and (RS)-S-[3-(bromomethyl)phenyl]-N-(ethoxycarbonyl)-S-ethylsulphoximide (108 mg, 0.32 mmol) are suspended in 5.0 mL of acetone. After addition of potassium carbonate (55 mg, 0.4 mmol), the reaction mixture is refluxed for 6 hours. The batch is diluted with ethyl acetate and the organic phase is washed with water and dried over sodium sulphate to leave, after removal of the solvent and also after chromatographic purification (silica gel, hexane/ethyl acetate: 0→100% ethyl acetate, followed by ethyl acetate/methanol: 9/1) the desired product in 62% yield (65 mg).

후처리

  1. temperaturethe reaction mixture is refluxed for 6 hours
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. customto leave
  5. customafter removal of the solvent
  6. customalso after chromatographic purification (silica gel, hexane/ethyl acetate: 0→100% ethyl acetate, followed by ethyl acetate/methanol: 9/1) the desired product in 62% yield (65 mg)

출처 및 근거

ORD 기록
ord-945f8c5d0cab40e6a992f2df6ccf371e
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863283B2

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