반응 #159670

반응 방정식

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

2-(2-benzylpyrrolidin-1-yl)-5-chloronicotinic acid

methyl 4-(1-aminocyclopropyl)benzoate

methyl 4-(1-aminocyclopropyl)benzoate hydrochloride

N,N-Diisopropylethylamine

→

title compound ( D144 )

수율 61.2%

methyl 4-(1-(2-(2-benzylpyrrolidin-1-yl)-5-chloronicotinamido)cyclopropyl)benzoate

수율 61.2%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출extracted with diethyl ether (3×15 ml)
3. 3
   세척The combined organic layers were washed with brine (2×10 ml)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The crude residue was purified by Biotage column (10 g)
8. 8
   세척eluting with a mixture dichloromethane/ethylacetate from 100/0 to 90/10
9. 9
   기타Collected fractions, after solvent evaporation

실험 절차

A mixture of 2-(2-benzylpyrrolidin-1-yl)-5-chloronicotinic acid (D100) (70 mg, 0.22 mmol), methyl 4-(1-aminocyclopropyl)benzoate (D7) (50.31 mg, 0.22 mmol) and N,N-Diisopropylethylamine (0.115 ml, 0.66 mmol) in dimethylformamide (5 ml) was stirred at room temperature for 1 h. (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) (137.9 mg, 0.265 mmol) was added and the resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-water and extracted with diethyl ether (3×15 ml). The combined organic layers were washed with brine (2×10 ml), dried over Na2SO4, filtered and concentrated. The crude residue was purified by Biotage column (10 g) eluting with a mixture dichloromethane/ethylacetate from 100/0 to 90/10. Collected fractions, after solvent evaporation, afforded the title compound (D144) (66 mg)

출처