3-Pyridinemethanamine → HCID 178512714, compound

Participants

Reaction Steps

A solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 7.0 g; 23 mmoles) in 180 ml of methanol was added dropwise to a partial suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (4.1 g; 23 mmoles) in 400 ml of methanol at 8°. This was followed by 3-picolylamine (2.74 g; 25.3 mmoles) and the reaction mixture was stirred at 8° for 15 minutes and at ambient temperature for 20 hours. The reaction solution was evaporated and the residue flash chromatographed on 125 g of silica gel (230-400 mesh) using CH3CN(90):CH3OH(10):NH4OH(0.5) as the eluant. A second purification by preparative high pressure liquid chromatography on silica with CH2Cl2 (85):95%EtOH(15):NH4OH(0.5) as the mobile phase yielded 0.78 g of the title compound as a buff-colored foam containing 0.4 mole of ethanol, mp 128°-138° (foaming).

Provenance & Evidence