2-Furancarbonyl chloride → HCID 20544870, compound

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A solution of 1-methyl-N5 -[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (A) (1.0 g) and 2-furancarboxylic acid, chloride (0.42 g) in pyridine (25 ml) was kept at ambient temperature for 1 h. The pyridine was evaporated in vacuo and the residue was azeotropically distilled with toluene to give an oil which was partitioned between ethyl acetate and 2 M hydrochloric acid. The pH of the aqueous extract was adjusted to pH 9 and it was extracted with ethyl acetate. The organic extracts were evaporated to a gum which was chromatographed on silica using ethyl acetate: methanol (9:1) to give the title compound (0.30 g) as a glassy solid. tlc System B, Rf 0.57. Nmr (CDCl3) 1.5,brs, (1H); 2.53,m, (1H); 2.75,t+m, (2H); 3.0-3.3,m, (3H); 3.5,dd (1H); 5.31,t, (1H); 5.92,t, (2H); 6.42,q, (2H); 6.50,s, (3H); 6.59,s, (3H); 7.6,brs; (4H); 7.9,m, (2H); 8.5,m, (6H).

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