4'-Mercaptoacetanilide → HCID 178418994, compound

HRID 480640Notes

Reaction equation

HRID 480640 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[C:9]([NH:11][C:12]2[NH:13][N:14]=[C:15]([CH3:17])[CH:16]=2)[CH:8]=[C:7]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:6]=1)(=O)=O.[C:24]([NH:27][C:28]1[CH:33]=[CH:32]C(S)=[CH:30][CH:29]=1)(=[O:26])[CH3:25]>C(O)(C)(C)C>[C:24]([NH:27][C:28]1[CH:33]=[CH:32][C:1]([S:2][C:5]2[N:10]=[C:9]([NH:11][C:12]3[NH:13][N:14]=[C:15]([CH3:17])[CH:16]=3)[CH:8]=[C:7]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:6]=2)=[CH:30][CH:29]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 707774'-MercaptoacetanilideHCID 178419103(2-methylsulfonyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine

Product 1

HCID 178418994HCID 178418994, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The above-prepared [2-methylsulfonyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (178 mg, 0.52 mmol) and 4-acetamidothiophenol (176 mg, 1.05 mmol) are refluxed in tert-butanol (5 mL) over 20 h. 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 residue is purified by flash chromatography to give the desired product [2-(4-acetamidophenylsulfanyl)-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

Workup

  1. custompartitioned between ethyl acetate and aqueous NaHCO3
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-7ce968f7914a4ac9b27c7a9612588a1f
Source dataset
uspto-grants-2003_11
Patent number
US06653301B2

Reaction notes

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