Réaction #1483039

Équation de réaction

tert-Butyl 2-((2-aminoethyl)(methyl)amino)ethylcarbamate

nicotinic acid

EDCI

→

tert-butyl 2-(methyl(2-(nicotinamido)ethyl)amino)ethylcarbamate

Rendement 30.3%

Solvants

CH3CN

EtOAc

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction mixture
2. 2
   LavageThe organic layer was washed with saturated aqueous NaHCO3, brine
3. 3
   Séchagedried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe resulting residue was purified by silica gel chromatography (5% MeOH—CH2Cl2)

Mode opératoire

tert-Butyl 2-((2-aminoethyl)(methyl)amino)ethylcarbamate (400 mg, 1.84 mmol) was taken up in CH3CN (10 mL) along with nicotinic acid (227 mg, 1.84 mmol) and EDCI (353 mg, 2.02 mmol). The resulting reaction mixture was stirred at room temperature for 18 h and then diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (5% MeOH—CH2Cl2) to afford tert-butyl 2-(methyl(2-(nicotinamido)ethyl)amino)ethylcarbamate (180 mg, 30%). MS calculated for C16H26N4O3: 322.2. found: [M+H]+ 323.

Source