4'-Mercaptoacetanilide → HCID 178418994, compound

HRID 1864604Notes

Reaction equation

HRID 1864604 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-b4247c1c33db4a64ac052dd33f5b56b2
Source dataset
uspto-grants-2009_12
Patent number
US07625913B2

Reaction notes

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