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【结 构 式】 
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【分子编号】44430 【品名】2-methoxy-5-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]benzonitrile 【CA登记号】 |
【 分 子 式 】C10H6F3N5O 【 分 子 量 】269.1859496 【元素组成】C 44.62% H 2.25% F 21.17% N 26.02% O 5.94% |
合成路线1
该中间体在本合成路线中的序号：(VIb)The reduction of 2-iodo-4-nitroanisole (I) with Fe and HOAc/HCl in methanol gives 4-amino-2-iodoanisole (II), which is acylated with trifluoroacetic anhydride and triethylamine to give the corresponding amide (III). The reaction of (III) with PPh3 and CCl4 affords the iminochloride (IV), which is cyclized with sodium azide in acetic acid, giving 1-(3-iodo-4-methoxyphenyl)-5-(trifluoromethyl)tetrazole (V). The reaction of (V) with 13C- or 14C-labeled zinc cyanide and palladium tetrakis triphenylphosphine in DMF yields the labeled benzonitrile (VI), which is treated with Raney-Ni and NaH2PO2 in pyridine/HOAc/water to afford the benzaldehyde (VII). Finally, this compound is reductocondensed with 2(S)-phenylpiperidin-3(S)-amine (VIII) by means of NaH(OAc)3 in dichloromethane.
| 【1】 Sutherland, D.R.; Cable, K.M.; Wells, G.N.; Synthesis of carbon-14 labelled NK-1 receptor antagonists GR203040 and GR205171. J Label Compd Radiopharm 2000, 43, 1, 29. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIc) | 22466 | 2-methoxy-5-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]benzaldehyde | C10H7F3N4O2 | 详情 | 详情 | |
| (VIa) | 44429 | 2-methoxy-5-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]benzonitrile | C10H6F3N5O | 详情 | 详情 | |
| (VIb) | 44430 | 2-methoxy-5-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]benzonitrile | C10H6F3N5O | 详情 | 详情 | |
| (VIIa) | 44431 | 2-methoxy-5-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]benzaldehyde | C10H7F3N4O2 | 详情 | 详情 | |
| (VIIb) | 44432 | 2-methoxy-5-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]benzaldehyde | C10H7F3N4O2 | 详情 | 详情 | |
| (VIc) | 44433 | 2-methoxy-5-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]benzonitrile | C10H6F3N5O | 详情 | 详情 | |
| (I) | 44424 | 2-iodo-1-methoxy-4-nitrobenzene; 2-iodo-4-nitrophenyl methyl ether | C7H6INO3 | 详情 | 详情 | |
| (II) | 44425 | 3-iodo-4-methoxyaniline; 3-iodo-4-methoxyphenylamine | C7H8INO | 详情 | 详情 | |
| (III) | 44426 | 2,2,2-trifluoro-N-(3-iodo-4-methoxyphenyl)acetamide | C9H7F3INO2 | 详情 | 详情 | |
| (IV) | 44427 | 2,2,2-trifluoro-N-(3-iodo-4-methoxyphenyl)ethanimidoyl chloride | C9H6ClF3INO | 详情 | 详情 | |
| (V) | 44428 | 1-(3-iodo-4-methoxyphenyl)-5-(trifluoromethyl)-1H-1,2,3,4-tetraazole; 2-iodo-4-[5-(trifluoromethyl)-1H-1,2,3,4-tetraazol-1-yl]phenyl methyl ether | C9H6F3IN4O | 详情 | 详情 | |
| (VIII) | 22467 | (2S,3S)-2-phenylpiperidinylamine; (2S,3S)-2-phenyl-3-piperidinamine | C11H16N2 | 详情 | 详情 |