Triethylamine → (S)-methyl 4-(1-(5-chloro-2-(3-(4-fluorophenoxy)azetidin-1-yl)nicotinamido)ethyl)benzoate

A mixture of 5-chloro-2-(3-(4-fluorophenoxy)azetidin-1-yl)nicotinic acid (D102) (75 mg, 0.232 mmol) 1-Hydroxybenzotriazole hydrate (31.34 mg, 0.232 mmol) and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (66.8 mg, 0.35 mmol) in dichloromethane (3 ml) was stirred 1 h at room temperature. A solution (S)-methyl 4-(1-aminoethyl)benzoate (D3) (50 mg, 0.232 mmol) and triethylamine (0.03 ml, 0.232 mmol) in dichloromethane (1 ml) was added and the resulting mixture was stirred overnight at room temperature. NaHCO3 sat. sol. (5 ml) was added and the mixture was extracted with dichloromethane (3×10 ml). Collected organics, after solvent evaporation were purified by SPE-Si (10 g) eluting with a mixture Cyclohexane/ethylacetate from 95/05 to 60/40. Collected fractions, after solvent evaporation, afforded the title compound (D146) (100 mg).

1. stirringthe resulting mixture was stirred overnight at room temperature
2. extractionthe mixture was extracted with dichloromethane (3×10 ml)
3. customCollected organics, after solvent evaporation
4. customwere purified by SPE-Si (10 g)
5. washeluting with a mixture Cyclohexane/ethylacetate from 95/05 to 60/40
6. customCollected fractions, after solvent evaporation

ORD-Eintrag

ord-e8a45cd97aca4db684d6ea6e5ec381f9

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08828987B2