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【结 构 式】 
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【分子编号】13970 【品名】2-(2-Naphthyl)acetyl chloride 【CA登记号】 |
【 分 子 式 】C12H9ClO 【 分 子 量 】204.65556 【元素组成】C 70.43% H 4.43% Cl 17.32% O 7.82% |
合成路线1
该中间体在本合成路线中的序号：(II)The condensation of 4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine (I) with 2-(2-naphthyl)acetyl chloride (II) by means of triethylamine in dichloromethane gives 1-[2-(2-naphthyl)acetyl]-4-[3-(trifluoromethyl)phenyl]-1,2,3,6 tetrahydropyridine (III), which is finally reduced with LiAlH4 in ethyl ether.
| 【1】 Castaner, J.; Mucke, H.A.M.; SR-57746A. Drugs Fut 1998, 23, 6, 616. |
| 【2】 Nisato, D.; Frigerio, M.; Miranda, G.F. (Midy SpA; Sanofi-Synthelabo ); Trifluoromethylphenyltetrahydropyridines with anorexigenic activity, a process for their preparation and compsns. EP 0101381 . |
合成路线2
该中间体在本合成路线中的序号：(II)2-(2-Naphthyl)acetic acid (I) is activated as the corresponding acid chloride (II) upon refluxing with SOCl2. Subsequent condensation of acid chloride (II) with N-methyl piperazine (III) affords the title amide.
| 【1】 Hayes, E.S. (Cardiome Pharma Corp.); Serotonin ligands as pro-erectile cpds.. WO 0028993 . |
| 【2】 Zolotoy, A.B.; Hayes, E.S. (Cardiome Pharma Corp.); Aroylpiperazines for modulating sexual activity. WO 9902159 . |
合成路线3
该中间体在本合成路线中的序号：(II)2-Naphthylacetic acid (I) was converted to the corresponding acid chloride (II) upon treatment with oxalyl chloride in the presence of a catalytic amount of DMF. Subsequent coupling of acid chloride (II) with N-methyl-3-aminobenzamide (III) in pyridine furnished the target diamide.
| 【1】 Kawamura, M.; Ando, R.; Chiba, N.; 3-(Arylacetylamino)-N-methylbenzamides: A novel class of selective anti-Helicobacter pylori agents. J Med Chem 2001, 44, 25, 4468. |
| 【2】 Ando, R.; et al.; 3-(Arylacetylamino)-N-methylbenzamides: New class of selective anti-Helicobacter pylori agents. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 248. |
| 【3】 Ando, R.; Watanabe, K.; Chiba, N.; Kawamura, M. (Mitsubishi Chemical Corp.); Amide derivs.. EP 0887341; JP 1999071336 . |