Benzoyl chloride → HCID 22319161, compound

HRID 229696Notes

Reaction equation

HRID 229696 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](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)(Cl)Cl>[C:36]([N:25]1[CH2:24][CH2:23][CH:22]([CH2:21][N:11]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:14]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])[C:10]2=[O:28])[CH2:27][CH2:26]1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22318995HCID 22318995, compound

Product 1

HCID 22319161HCID 22319161, compoundYield 65.1%

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 19 mg of benzoyl 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 25 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-3f7bf59d988643408e077dd298604864
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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