Methanesulfonyl chloride → N-{4-[1-(4-Chloro-2-methyl-phenyl)-3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-propyl]-phenyl}-methanesulfonamide

HRID 1617954Notes

Reaction equation

HRID 1617954 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[CH3:27])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:3][CH:4]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[C:21]([CH3:27])[CH:22]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 666687055-[3-(4-Amino-phenyl)-3-(4-chloro-2-methyl-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 67015741N-{4-[1-(4-Chloro-2-methyl-phenyl)-3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-propyl]-phenyl}-methanesulfonamideYield 64.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 10 mL round-bottomed flask 5-[3-(4-amino-phenyl)-3-(4-chloro-2-methyl-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one (88 mg) and methanesulfonyl chloride (40.1 mg) were combined with pyridine (0.87 mL) to give a brown solution. The reaction mixture was stirred at room temperature for 3 h. The crude reaction mixture was concentrated in vacuo. The reaction mixture was extracted 3× with ethyl acetate, the organic layers were washed 3× with water and dried over magnesium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 0% to 10% methanol in dichloromethane) to give the title compound (68 mg) as a colourless foam, MS (ESI+): m/z=459.3 [M+H]+.

Workup

  1. customto give a brown solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. extractionThe reaction mixture was extracted 3× with ethyl acetate
  5. washthe organic layers were washed 3× with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 20 g, 0% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7140605662924ac6a7c7c1ff02fcbb07
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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