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

HRID 7612

반응식

HRID 7612 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-2c9f0fe041d94e3aa4d71ea144b51227
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087603B2

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