Réaction #159668

Équation de réaction

benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate

5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinic acid

methyl 4-(1-aminocyclopropyl)benzoate hydrochloride

N,N-Diisopropylethylamine

→

title compound ( D142 )

Rendement 79.4%

methyl 4-(1-(5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate

Rendement 79.4%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (2×20 ml)
2. 2
   LavageThe organic solution was washed with brine (40 ml)
3. 3
   Séchagedried over Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   Autreto obtain a residue which
6. 6
   Autrewas purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate (4:1)
7. 7
   AutreCollected fractions after solvent evaporation

Mode opératoire

A solution of 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinic acid (D98) (150 mg, 0.5 mmol), methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (114 mg, 0.5 mmol) and N,N-Diisopropylethylamine (194 mg, 1.5 mmol) in dimethylformamide (10 ml) was stirred 1 h at room temperature, then benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (312 mg, 0.6 mmol) was added. The mixture was stirred at room temperature overnight, then poured into ice-water (20 ml) and extracted with ethyl acetate (2×20 ml). The organic solution was washed with brine (40 ml), dried over Na2SO4 and concentrated to obtain a residue which was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate (4:1). Collected fractions after solvent evaporation afforded the title compound (D142) (189 mg) as a yellow solid.

Source