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

HRID 249978ノート

反応式

HRID 249978 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-945f8c5d0cab40e6a992f2df6ccf371e
出典データセット
uspto-grants-2011_01
特許番号
US07863283B2

反応ノート

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