Famotidine, MK-208, YM-11170, Quamatel, Pepdine, Famodil, Gastridin, Pepcid RPD, Pepcid AC, Pepcid, Pepdul, Pepcidine, Gaster

合成路线:The reaction ot S-(2-aminothiazol-4-ylmethyl)isothiourea (I) with 3-chloropropionitrile (II) by means of NaOH in ethanol - water gives 3-(2-aminothiazol-4-ylmethylthio)propionitrile (III),which is condensed with benzoyl isothiocyanate (IV) in refluxing acetone to afford 3-[2-(3-benzoylthioureido)thiazol-4-ylmethylthio]propionitrile (V).The hydrolysis of (V) with K2CO3 in acetone - methanol - water yields 3-(2-thioureidothiazonl-4-ylmethylthio)propionitrile (VI),which by methylation with methyl iodide in refluxing ethanol is converted into 3-[2-(S-methylisothioureido)thiazol-4-ylmethylthio]propionitrile hydroiodide (VII).The reaction of (VII) with NH3 and NH4Cl in methanol at 90 C in a pressure vessel affords 3-(2-guanidinothiazol-4-ylmethylthio)propionitrile (VIII),which by partial alcoholysis with methanol by means of dry HCl in CHCl3 is converted into methyl 3-(2-guanidinothiazol-4-ylmethylthio)propionimidate (IX).Finally,this compound is treated with sulfamide in refluxing methanol.

参考文献标题:Novel amidine derivative and its preparation
文献作者:Hirata,Y.; et al.(Yamanouchi Pharmaceutical Co.,Ltd.)
参考来源:BE 0882071; DE 2951675; DE 3008056; FR 2450827; GB 2052478; GB 2055800; JP 55118476; NL 7909321; NL 8001361


合成路线:The reaction ot S-(2-aminothiazol-4-ylmethyl)isothiourea (I) with 3-chloropropionitrile (II) by means of NaOH in ethanol - water gives 3-(2-aminothiazol-4-ylmethylthio)propionitrile (III),which is condensed with benzoyl isothiocyanate (IV) in refluxing acetone to afford 3-[2-(3-benzoylthioureido)thiazol-4-ylmethylthio]propionitrile (V).The hydrolysis of (V) with K2CO3 in acetone - methanol - water yields 3-(2-thioureidothiazonl-4-ylmethylthio)propionitrile (VI),which by methylation with methyl iodide in refluxing ethanol is converted into 3-[2-(S-methylisothioureido)thiazol-4-ylmethylthio]propionitrile hydroiodide (VII).The reaction of (VII) with NH3 and NH4Cl in methanol at 90 C in a pressure vessel affords 3-(2-guanidinothiazol-4-ylmethylthio)propionitrile (VIII),which by partial alcoholysis with methanol by means of dry HCl in CHCl3 is converted into methyl 3-(2-guanidinothiazol-4-ylmethylthio)propionimidate (IX).Finally,this compound is treated with sulfamide in refluxing methanol.
参考文献标题:Famotidine
文献作者:Blancafort,P.; Castar,J.; Hillier,K.; Serradell,M.N.
参考来源:Drugs Fut 1983,8(1),14


产品链接: CAS No. 76824-35-6››