Benzylamine → N-benzyl-2-(2-(phenylsulfonyl)ethylthio)nicotinamide
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]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH2:34]([NH:41][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]=1Participants
5
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 h at RT. A solution of 82 mg (0.77 mmol) of benzylamine in DCM (6 ml) was then added, and stirring was continued for a further 16 hours at RT. The reaction solution was then washed in each case three times with a sat. aq. ammonium chloride solution and saturated aqueous NaHCO3 solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. 266 mg (0.64 mmol, 83%) of N-benzyl-2-(2-(phenylsulfonyl)ethylthio)nicotinamide were obtained as residue.
Workup
- stirringstirring
- waitwas continued for a further 16 hours at RT
- washThe reaction solution was then washed in each case three times with a sat. aq. ammonium chloride solution and saturated aqueous NaHCO3 solution
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-02a347cb505c4ab6b09391e9c3f019eb
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084470B2
Reaction notes
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