Methylamine → 1-[5-(2-[2-(2,2,2-Trifluoroethyl)guanidino]thiazol-4-yl)pentylamino]-2-methylaminocyclobutene-3,4-dione

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A mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(5-aminopentyl)thiazole (0.3 g.) and 1,2-dimethoxycyclobutene-3,4-dione (0.15 g.) in methanol (3 ml.) was allowed to stand at room temperature for 4 hours. Ethanolic methylamine (33% w/v, 20 ml.) was then added and the solution allowed to stand overnight. The mixture was evaporated to dryness and the residue purified by preparative thin layer chromatography using ethyl acetate/methanol/water 6:1:1 v/v/v as developing solvent to give 1-[5-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)pentylamino]-2-methylaminocyclobutene-3,4-dione as colourless gum (0.17 g.). The n.m.r. spectrum of the hydrogen maleate salt in d6 dimethylsulphoxide using tetramethylsilane as internal standard (δ=0) included the following resonances (67 ): 1.5 (multiplet, 6H); 2.6 (multiplet, 2H); 3.1 (doublet, 3H); 3.5 (multiplet, 2H); 4.1 (multiplet, 2H); 6.55 (singlet, 1H).

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