Benzenesulfonyl chloride → HCID 22319171, compound

HRID 497860Notes

Reaction equation

HRID 497860 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([CH2:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].C(N(CC)CC)C.[C:36]1([S:42](Cl)(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)(Cl)Cl>[C:36]1([S:42]([N:25]2[CH2:24][CH2:23][CH:22]([CH2:21][N:11]3[CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[CH:14]=[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:1]#[N:2])[C:10]3=[O:28])[CH2:27][CH2:26]2)(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 22318995HCID 22318995, compound

Product 1

HCID 22319171HCID 22319171, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

30 mg of 3-(2-cyanophenyl)-1-(piperidin-4-yl)methyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 2 ml of chloroform. Under ice-cooling, 0.04 ml of triethylamine and 23 mg of benzenesulfonyl chloride were added thereto, followed by stirring at room temperature for 2 hours. The reaction solution was diluted with chloroform, and washed with a saturated aqueous solution of sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate, and then evaporated and the residue was purified by silica gel chromatography (ethyl acetate/hexane), to give 30 mg of the title compound.

Workup

  1. temperatureUnder ice-cooling
  2. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a2f9c137aa6d49eea8c90443f4c5a622
Source dataset
uspto-grants-2005_09
Patent number
US06949571B2

Reaction notes

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