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【结 构 式】

【药物名称】Amitivir, LY-217896

【化学名称】1,3,4-Thiadiazol-2-ylcyanamide
      2-(Cyanamino)-1,3,4-thiadiazole

【CA登记号】111393-84-1, 111393-93-2 (Na salt)

【 分 子 式 】C3H2N4S

【 分 子 量 】126.14019

【开发单位】Lilly (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs

合成路线1

The synthesis of LY-217896 and its [5-14C]- and uniformly labeled [UL-13C]-isotopomers has been described: The cyclization of thiosemicarbazide (I) with formic acid (II) at 80-90 C gives 2-amino-1,3,4-thiadiazole (III), which is protected with benzyl chloride in refluxing isopropanol to yield 3-benzyl-1,3,4-thiadiazol-2(3H)-imine (IV). The reaction of (IV) with cyanogen bromide by means of NaHCO3 in methanol - water affords N-(3-benzyl-1,3,4-thiadiazol-2(3H)-ylidene)cyanamide (V), which is finally deprotected with AlCl3 in dichloromethane. The [5-14C]-isotopomer is obtained using [14C]-labeled formic acid in the first step of the synthesis, and the [UL-13C]-isotopomer is obtained using [13C]-labeled thiosemicarbazide (I) and [13C]-formic acid. [13C]-Labeled (I) is synthesized by reaction of potassium cyanide-[13C] with sulfur, yielding potassium thiocyanate-[13C], which is reacted with hydrazine to give [13C]-thiosemicarbazide.

1 Wheeler, W.J.; Blanchard, W.B.; The synthesis of 1,3,4-thiadiazol-2-ylcyanamide sodium, a potentially useful anti-influenza agent and its [5-14C] and [UL-13C3] isotopomers. J Label Compd Radiopharm 1992, 31, 7, 495.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 12954 1-Hydrazinecarbothioamide; Thiosemicarbazide 79-19-6 CH5N3S 详情 详情
(II) 14590 Formic acid 64-18-6 CH2O2 详情 详情
(III) 14591 2-Amino-1,3,4-thiadiazole; 1,3,4-Thiadiazol-2-amine; 1,3,4-Thiadiazol-2-ylamine 4005-51-0 C2H3N3S 详情 详情
(IV) 14592 3-benzyl-1,3,4-thiadiazol-2(3H)-imine C9H9N3S 详情 详情
(V) 14593 N-[3-benzyl-1,3,4-thiadiazol-2(3H)-ylidene]cyanamide C10H8N4S 详情 详情
Extended Information