Reaktion #2012736

Reaktionsgleichung

EDC hydrochloride

HOBT

DIPEA

pyridin-2-yl-methanamine

2-(3-(4-fluorophenyl)-propylthio)nicotinic acid

→

2-[3-(4-fluorophenyl)-propylsulfanyl]-N-(pyridin-2-yl-methyl)-pyridine-3-carboxylic acid amide

Ausbeute 46.0%

Lösungsmittel

hexane EA

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionDilution with water (40 ml) and extraction with DCM (3×50 ml)
2. 2
   WaschenThe combined organic phases were washed with a sat. NH4Cl sol. and water
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo

Vorschrift

520 mg (2.74 mmol) of EDC hydrochloride, 250 mg (1.64 mmol) of HOBT, 0.9 ml (5.48 mmol) of DIPEA and 180 mg (1.64 mmol) of pyridin-2-yl-methanamine were added in succession to a solution of 400 mg (1.37 mmol) of 2-(3-(4-fluorophenyl)-propylthio)nicotinic acid in DCM (6 ml), and the mixture was stirred for 4 h at RT. Dilution with water (40 ml) and extraction with DCM (3×50 ml) were then carried out. The combined organic phases were washed with a sat. NH4Cl sol. and water, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 22:3) of the residue yielded 240 mg (0.63 mmol, 46%) of 2-[3-(4-fluorophenyl)-propylsulfanyl]-N-(pyridin-2-yl-methyl)-pyridine-3-carboxylic acid amide. MS: m/z 382.1 [M+H]+.

Quelle