Reaktion #159689

Reaktionsgleichung

5-chloro-2-(3-((4-fluorophenoxy)methyl)azetidin-1-yl)nicotinic acid

O-(6-Chlorobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride

methyl 4-(1-aminocyclopropyl)benzoate hydrochloride

→

title compound ( D163 )

Ausbeute 64.1%

methyl 4-(1-(5-chloro-2-(3-((4-fluorophenoxy)methyl)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate

Ausbeute 64.1%

Lösungsmittel

NH4Cl

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred overnight at room temperature
2. 2
   Extraktionthe mixture was extracted with ethylacetate (3×10 ml)
3. 3
   SonstigeThe residue obtained
4. 4
   Sonstigeafter solvent evaporation
5. 5
   Sonstigewas purified by SPE-Si cartridge (10 g)
6. 6
   Wascheneluting dichloromethane
7. 7
   SonstigeCollected fractions, after solvent evaporation

Vorschrift

A mixture of 5-chloro-2-(3-((4-fluorophenoxy)methyl)azetidin-1-yl)nicotinic acid (D113) (55.4 mg, 0.161 mmol), O-(6-Chlorobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HCTU) (66.8 mg, 0.161 mmol) and N,N-disopropylethylamine (0.072 ml, 0.403 mmol) was stirred 30 min at room temperature. Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (37.8 mg, 0.161 mmol) was added and the reaction mixture stirred overnight at room temperature. NH4Cl saturated solution (20 ml) was added and the mixture was extracted with ethylacetate (3×10 ml). The residue obtained after solvent evaporation was purified by SPE-Si cartridge (10 g) eluting dichloromethane. Collected fractions, after solvent evaporation, afforded the title compound (D163) (52.6 mg).

Quelle