4-Methylmorpholine → N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide

Participants

Reaction Steps

4.82 g (15.0 mmol) of TBTU and 3.54 g (35 mmol) of N-methyl-morpholine were added to a solution of 1.55 g (10.0 mmol) of 2-mercapto-nicotinic acid in DMF (30 ml), and the mixture was stirred for 30 min at RT. 1.25 g (10.0 mmol) of bicyclo-[2.2.1]heptan-2-ylmethanamine were then added, and stirring was carried out for 16 h at RT. The mixture was then diluted with EA and washed with sat. aq. NH4Cl sol., a 1N aq. NaHCO3 sol. and brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (DCM/MeOH 99:1) of the residue yielded 308 mg 1.39 g (5.3 mmol, 53%) of N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide.

Provenance & Evidence