CNS-1102

A solution of m-ethylphenylcyanamide (1.46 g, 10 mmol) and sodium hydride (480 mg, 20 mmol, prewashed with hexane) in anhydrous THF (10 ml) was heated at 80-85°C for 2.5 hours. After it was allowed to cool to room temperature, methyl iodide (3.5 g, 25 mmol) was added and stirring continued at room temperature for 2 hours. Methanol (10 ml) followed by water (20 ml) was added and the reaction mixture was extracted with dichloromethane (3x25 ml). Concentration of the organic layer followed by flash chromatography on SiO2 afforded N-(m-ethylphenyl)-N-methylcyanamide (960 mg, 60%) as a colorless liquid: IR (film): 2220, 3400cm-1. A mixture of m-ethylphenyl-N-methylcyanamide (520 mg, 3.25 mmol) and 1- aminonaphthalene hydrochloride (508 mg, 3.25 mmol) was placed in a preheated oil bath at 160°C for 3 hours and then allowed to cool to room temperature. The resulting solid was taken into dichloromethane and washed with 10% sodium hydroxide solution. The organic layer was concentrated and the resulting residue was dissolved in absolute ethanol (2 ml) and treated with dilute hydrochloric acid. It was concentrated and the solid was twice recrystallized from absolute ethanol-ether to give N-(1-naphthyl)-N'-(methylphenyl)- N'-methylguanidine hydrochloride (403 mg, 37%) as off-white needles, melting point 223-225°C.

Stroke and traumatic brain injury treatment (NMDA ion channel blocker).

Molecular Weight:339.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:339.1502254
Monoisotopic Mass:339.1502254
Topological Polar Surface Area:41.6
Heavy Atom Count:24
Complexity:406
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes