5-chloro-2-(1H-1,2,3,4-tetraazol-1-yl)benzonitrile -Drug Synthesis Database

【结构式】

【分子编号】63211

【品名】5-chloro-2-(1H-1,2,3,4-tetraazol-1-yl)benzonitrile

【CA登记号】

【分子式】C₈H₄ClN₅

【分子量】205.60616

【元素组成】C 46.73% H 1.96% Cl 17.24% N 34.06%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The precursor 5-chloro-2-tetrazol-1-yl-benzylamine (V) is prepared as follows. Cyclization of 5-chloroanthranilic acid (I) with sodium azide and trimethyl orthoformate gives rise to the tetrazole derivative (II). Subsequent coupling of acid (II) with ammonium chloride in the presence of EDC and HOAt affords amide (III). This is then dehydrated to the nitrile (IV) employing the Burgess reagent in THF. Nitrile (IV) is reduced to the target amine (V) by catalytic hydrogenation over Raney nickel.

参考文献中间体

合成目标

【1】 Williams, P.D.; Selnick, H.G.; Young, M.B.; Nantermet, P.G. (Merck & Co., Inc.); Thrombin inhibitors. EP 1359913; WO 0264140 .

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)	10285	2-Amino-5-chlorobenzoic acid	635-21-2	C₇H₆ClNO₂	详情	详情
(II)	63209	5-chloro-2-(1H-1,2,3,4-tetraazol-1-yl)benzoic acid		C₈H₅ClN₄O₂	详情	详情
(III)	63210	5-chloro-2-(1H-1,2,3,4-tetraazol-1-yl)benzamide		C₈H₆ClN₅O	详情	详情
(IV)	63211	5-chloro-2-(1H-1,2,3,4-tetraazol-1-yl)benzonitrile		C₈H₄ClN₅	详情	详情
(V)	63212	[5-chloro-2-(1H-1,2,3,4-tetraazol-1-yl)phenyl]methanamine; 5-chloro-2-(1H-1,2,3,4-tetraazol-1-yl)benzylamine		C₈H₈ClN₅	详情	详情

Extended Information