4H-1,2,4-triazol-4-amine; 4-Amino-4H-1,2,4-triazole; 4H-1,2,4-triazol-4-ylamine; 4-Amino-1,2,4-triazole -Drug Synthesis Database

【结构式】

【分子编号】16106

【品名】4H-1,2,4-triazol-4-amine; 4-Amino-4H-1,2,4-triazole; 4H-1,2,4-triazol-4-ylamine; 4-Amino-1,2,4-triazole

【CA登记号】584-13-4

【分子式】C₂H₄N₄

【分子量】84.08072

【元素组成】C 28.57% H 4.8% N 66.63%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The arylation of 1,2,4-triazol-4-amine (I) with 4-fluorobenzonitrile (II) by means of NaH in DMSO gives 4-(1,2,4-triazol-4-ylamino)benzonitrile (III), which is then condensed with 4-bromobenzyl bromide (III) by means of K2CO3 in acetonitrile.

参考文献中间体

合成目标

【1】 Mealy, N.; Castaner, J.; YM-511. Drugs Fut 1996, 21, 7, 716.
【2】 Okada, M.; Kawaminami, E.; Yoden, T.; Kudo, M.; Isomura, Y. (Yamanouchi Pharmaceutical Co., Ltd.); Triazolylated tertiary amine cpds. or salts thereof. EP 0641785; JP 1993505096; US 5674886; WO 9305027 .

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)	16106	4H-1,2,4-triazol-4-amine; 4-Amino-4H-1,2,4-triazole; 4H-1,2,4-triazol-4-ylamine; 4-Amino-1,2,4-triazole	584-13-4	C₂H₄N₄	详情	详情
(II)	14144	4-Fluorobenzonitrile	1194-02-1	C₇H₄FN	详情	详情
(III)	16108	4-(4H-1,2,4-triazol-4-ylamino)benzonitrile		C₉H₇N₅	详情	详情
(IV)	16109	1-bromo-4-(bromomethyl)benzene; 4-Bromobenzyl bromide	589-15-1	C₇H₆Br₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XII)

3) The condensation of 4-nitrobenzyl bromide (VI) with 4-amino-1,2,4-triazole (XII) in refluxing isopropanol gives 4-amino-1-(3-nitrobenzyl)-1,2,4-triazolium bromide (XIII), which is deaminated with NaNO2/HCl to afford 1-(4-nitrobenzyl)-1,2,4-triazole (VIII). The reduction of (VIII) yields amine (I), which by diazotation and reduction with Na2SO3 yields the corresponding hydrazine (IX). Finally, (IX) is cyclized with 4-(dimethylamino)butanal dimethylacetal (XIV) in acidic water.

参考文献中间体

合成目标

【1】 Castañer, J.; Mealy, N.; Rabassseda, X.; MK-0462. Drugs Fut 1995, 20, 7, 676.
【2】 Baker, R.; Pitt, K.G.; Matassa, V.G.; Storey, D.E.; Olive, C.; Street, L.J. (Merck Sharp & Dohme Ltd.); The sulphate salt of a substd. triazole, pharmaceutical compsns. thereof, and their use in therapy. EP 0573221; US 5527817; WO 9325547 .

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)	16680	methyl (2S)-2-(acetylsulfanyl)propanoate		C₆H₁₀O₃S	详情	详情
(VI)	16866	1-(Bromomethyl)-4-nitrobenzene; para-Nitrobenzyl bromide	100-11-8	C₇H₆BrNO₂	详情	详情
(VIII)	16868	1-(4-nitrobenzyl)-1H-1,2,4-triazole		C₉H₈N₄O₂	详情	详情
(XI)	16869	1-(4-hydrazinobenzyl)-1H-1,2,4-triazole		C₉H₁₁N₅	详情	详情
(XII)	16106	4H-1,2,4-triazol-4-amine; 4-Amino-4H-1,2,4-triazole; 4H-1,2,4-triazol-4-ylamine; 4-Amino-1,2,4-triazole	584-13-4	C₂H₄N₄	详情	详情
(XIII)	16873	4-amino-1-(4-nitrobenzyl)-1H-1,2,4-triazol-4-ium bromide	6085-99-0	C₉H₁₀BrN₅O₂	详情	详情
(XIV)	16874	N-(4,4-dimethoxybutyl)-N,N-diethylamine; N,N-diethyl-4,4-dimethoxy-1-butanamine		C₁₀H₂₃NO₂	详情	详情

Extended Information