Ethyl Acetate → 4-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester

HRID 605356ノート

反応式

HRID 605356 の反応式
[C:1]([C:3]1[C:4]([N:10]=[CH:11][N:12](C)C)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1)#[N:2].[CH3:15][O:16][C:17](=[O:40])[C:18]1[CH:23]=[CH:22][C:21]([S:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:27][CH:26]=2)=[C:20](N)[CH:19]=1.CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>CC(O)=O.O>[CH3:15][O:16][C:17](=[O:40])[C:18]1[CH:19]=[CH:20][C:21]([S:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])=[CH:27][CH:26]=2)=[C:22]([NH:2][C:1]2[C:3]3[CH:8]=[CH:7][C:6]([CH3:9])=[N:5][C:4]=3[N:10]=[CH:11][N:12]=2)[CH:23]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 59376792Methyl 3-amino-4-((4-((tert-butoxycarbonyl)amino)phenyl)thio)benzoateHCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

生成物 1

HCID 670403334-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester収率 62%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A suspension of N′-(3-cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine (1.00 g, 5.3 mmol) and 3-amino-4-(4-tert-butoxycarbonylamino-phenylsulfanyl)-benzoic acid methyl ester (prepared in Example 385C) (1.99 g, 5.3 mmol) in AcOH (20 mL) was heated at 120° C. for 30 minutes under N2. After cooling to room temperature, the reaction mixture was portioned between AcOEt (250 mL) and H2O (200 mL), and then made basic to pH 9 with K2CO3 under stirring. The organic layer was separated, washed with 10% NaHCO3, H2O and brine, dried over MgSO4, and evaporated to give pale brown oil. The oily residue was separated by silica gel column chromatography (AcOEt) to yellow amorphous, which was solidified by the treatment of i-Pr2O. The resulting solid was collected by filtration, washed with i-Pr2O, and dried at 40° C. overnight under reduced pressure to give the title compound as pale yellow crystal (1.70 g, 62%).

後処理

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was separated
  3. washwashed with 10% NaHCO3, H2O and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give pale brown oil
  7. customThe oily residue was separated by silica gel column chromatography (AcOEt) to yellow amorphous, which
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with i-Pr2O
  10. customdried at 40° C. overnight under reduced pressure

出典と根拠

ORDレコード
ord-7140ee43438d41a5a5c04c4563884bce
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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