1,1'-Carbonyldiimidazole → N-(cyclohexylmethyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide

HRID 660055Notes

Reaction equation

HRID 660055 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]1([S:19]([CH2:22][CH2:23][S:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([OH:29])=O)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:34]1([CH2:40][NH2:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(Cl)Cl>[CH:34]1([CH2:40][NH:41][C:27](=[O:29])[C:26]2[CH:30]=[CH:31][CH:32]=[N:33][C:25]=2[S:24][CH2:23][CH2:22][S:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:20])=[O:21])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 76688CyclohexanemethylamineHCID 28213502-[2-(Phenylsulfonyl)ethylthio]nicotinic acid

Product 1

HCID 25221518N-(cyclohexylmethyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamideYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

264 mg (1.62 mmol) of CDI were added to a solution of 500 mg (1.55 mmol) of 2-(2-(phenylsulfonyl)ethylthio)nicotinic acid in DCM (12 ml), and the mixture was stirred for 1 h at RT. A solution of 200 μl (1.55 mmol) of cyclohexanemethylamine in DCM (12 ml) was then added, and stirring was continued for a further 16 h at RT. The reaction solution was then washed in each case three times with sat. aq. ammonium chloride solution and saturated aqueous NaHCO3 solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. 624 mg (1.49 mmol, 96%) of N-(cyclohexylmethyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide were obtained as residue.

Workup

  1. stirringstirring
  2. waitwas continued for a further 16 h at RT
  3. washThe reaction solution was then washed in each case three times with sat. aq. ammonium chloride solution and saturated aqueous NaHCO3 solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95654f5e65a743efaeb815581542076d
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Reaction notes

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