N-Methylbenzylamine → N-benzyl-N-methyl-2-(2-(phenylsulfonyl)ethylthio)nicotinamide

HRID 660054Notes

Reaction equation

HRID 660054 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.[CH2:34]([NH:41][CH3:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH2:34]([N:41]([CH3:42])[C:27](=[O:29])[C:26]1[CH:30]=[CH:31][CH:32]=[N:33][C:25]=1[S:24][CH2:23][CH2:22][S:19]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:20])=[O:21])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 28213502-[2-(Phenylsulfonyl)ethylthio]nicotinic acid

Product 1

HCID 25221517N-benzyl-N-methyl-2-(2-(phenylsulfonyl)ethylthio)nicotinamideYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

132 mg (0.81 mmol) of CDI were added to a solution of 250 mg (0.77 mmol) of 2-(2-(phenylsulfonyl)ethylthio)nicotinic acid in DCM (6 ml), and the mixture was stirred for 1 hour at RT. A solution of 93 mg (0.77 mmol) of N-benzyl-N-methylamine in DCM (6 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. CC with the residue (DCM→DCM/MeOH 99.5:0.5) yielded 152 mg (0.36 mmol, 46%) of N-benzyl-N-methyl-2-(2-(phenylsulfonyl)ethylthio)nicotinamide.

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-b3877c58101e464f880a334d7caee8b1
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Reaction notes

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