Ammonia → 4-[6-(2-[2,2,2-Trifluoroethyl]guanidino)pyrid-2-ylthio]butyramide

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Reaction Steps

A solution of 4-[6-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-2-ylthio]butyric acid (84 mg.) and triethylamine (0.2 ml.) in DMF (5 ml.) was stirred at 0° while isobutylchloroformate (68 mg.) was added. The solution was kept at 0° for 0.5 hours, treated with a saturated solution of ammonia in EtOH (1 ml.) and then stirred at room temperature for 18 hours. The solution was evaporated to dryness and the residue partitioned between N aqueous HCl and EtOAc. The aqueous phase was basified with 10 N aqueous NaOH and extracted with EtOAc, and the extract was dried and evaporated to dryness to give 4-[6-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-2-ylthio]butyramide (60 mg.) which was crystallised as the hydrogen maleate salt from acetone, m.p. 138°-141°.

Provenance & Evidence