4'-Mercaptoacetanilide → N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-phenylpyrimidin-2-ylthio)phenyl)acetamide

HRID 7612

反応式

HRID 7612 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[C:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=1)(=[O:23])[CH3:22]>C(O)(C)(C)C>[C:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([S:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=3)[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)=[CH:27][CH:26]=1)(=[O:23])[CH3:22]

参加物

4

反応物 2

HCID 707774'-MercaptoacetanilideHCID 178418761(2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine

生成物 1

HCID 178419061N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-phenylpyrimidin-2-ylthio)phenyl)acetamide収率 85%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

The above prepared (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine. (60 mg, 0.21 mmol) is combined with 4-acetamidothiophenol (176 mg, 1.05 mmol) in tert-butanol (5 mL) and the mixture heated at reflux for 20 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and aqueous NaHCO3. The organic layer is washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue is purified by flash chromatography (SiO2, DCM/MeOH gradient) to afford [2-(4-acetamido-phenylsulfanyl)-6-phenyl-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (74 mg, 85%)

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 20 hours
  3. custompartitioned between ethyl acetate and aqueous NaHCO3
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified by flash chromatography (SiO2, DCM/MeOH gradient)

出典と根拠

ORDレコード
ord-2c9f0fe041d94e3aa4d71ea144b51227
出典データセット
uspto-grants-2006_08
特許番号
US07087603B2

関連ノート

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