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【结 构 式】 
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【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% |
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.
| 【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.
| 【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 |