[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([C:15](=O)[N:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3].B#B.Cl>O1CCCC1.O>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]To a stirred solution of 676 mg. (2.43 mmole) of 2-guanidino-4-(5-[N,N-dimethylcarbamoyl]-2-furyl)thiazole in 25 ml. of tetrahydrofuran was added dropwise, at room temperature, 24.9 ml. (24.3 mmole) of a 0.97M solution of diborane in tetrahydrofuran. Stirring was continued for 5 hours at room temperature and then 15 ml. of 6N hydrochloric acid was added slowly, keeping the temperature below 30° C. Stirring was continued for 30 minutes, and then the mixture was diluted with water and washed with ethyl acetate. The resulting aqueous phase was made alkaline with 1N sodium hydroxide solution and the solid which precipitated was recovered by filtration, to give 340 mg. of the title compound, mp greater than 200° C.
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