|
【结 构 式】 
|
【分子编号】30380 【品名】6-methyl-2-pyridinecarboxylic acid 【CA登记号】934-60-1 |
【 分 子 式 】C7H7NO2 【 分 子 量 】137.13812 【元素组成】C 61.31% H 5.14% N 10.21% O 23.33% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 6-methylpyridine-2-carboxylic acid (I) with refluxing SOCl2 gives 6-methylpyridine-2-carbonyl chloride (II), which is condensed with 5-aminotetrazole (III) by means of triethylamine in hot DMF.
| 【1】 Takeda, M.; Honma, Y.; Tsuzurahara, K.; 2-Pyridinecarboxamide derivatives compositions containing same and method of using same. EP 0053789; ES 8303398; JP 1482289C; JP 57095984; US 4404214 . |
| 【2】 Takeda, M.; Sekine, Y.; Ono, Y.; Hashiyama, T.; Honma, Y.; Tsuzurahara, K.; Hanamoto, K.; Antiallergic agents. 3. N-(1H-Tetrazol-5-yl)-2-pyridinecarboxamides. J Med Chem 1984, 27, 2, 125-128. |
| 【3】 Serradell, M.N.; Castaner, J.; TA-5707. Drugs Fut 1984, 9, 7, 527. |
| 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) | 30380 | 6-methyl-2-pyridinecarboxylic acid | 934-60-1 | C7H7NO2 | 详情 | 详情 |
| (II) | 34352 | 6-methyl-2-pyridinecarbonyl chloride | C7H6ClNO | 详情 | 详情 | |
| (III) | 14092 | 1H-1,2,3,4-Tetraazol-5-ylamine; 1H-Tetrazol-5-amine; 1H-1,2,3,4-Tetraazol-5-amine; 5-Amino-1H-1,2,3,4-tetrazole | 4418-61-5 | CH3N5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)Hydrogenation of 6-methylpyridine-2-carboxylic acid (I) over Pd/C in aqueous ammonia afforded the corresponding piperidine (II). Subsequent condensation of (II) with isovaleraldehyde (III), followed by catalytic hydrogenation with Pd/C provided the N-isopentyl piperidine (IV), which was finally coupled with O-benzyltyrosine tert-butyl ester (V) in the presence of benzotriazolyl tetramethyluronium hexafluorophosphate (HBTU) to furnish the target amide.
| 【1】 Szoke, B.G.; Hu, L.-Y.; Millerman, E.; Nikam, S.S.; Rafferty, M.F.; Ryder, T.R.; Synthesis and biological evaluation of substituted 4-(OBz)phenylalanine derivatives as novel N-type calcium channel blockers. Bioorg Med Chem Lett 1999, 9, 8, 1121. |
| 【2】 Hu, L.-Y.; et al.; PD 151307 analogs: Synthesis and biological evaluation of substituted 4-(OBz)phenylalanine derivatives as novel N-type calcium channel blockers. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 119. |
| 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) | 30380 | 6-methyl-2-pyridinecarboxylic acid | 934-60-1 | C7H7NO2 | 详情 | 详情 |
| (II) | 30381 | 6-methyl-2-piperidinecarboxylic acid | C7H13NO2 | 详情 | 详情 | |
| (III) | 26052 | 3-methylbutanal | 590-86-3 | C5H10O | 详情 | 详情 |
| (IV) | 30382 | 1-isopentyl-6-methyl-2-piperidinecarboxylic acid | C12H23NO2 | 详情 | 详情 | |
| (V) | 26717 | tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoate | C20H25NO3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)6-Methylpicolinic acid (I) is esterified with MeOH and H2SO4, and the resultant methyl ester (II) is further reacted with methylamine to afford amide (III). The target zinc complex is then obtained by treatment of picolinamide (III) with an aqueous solution of ZnSO4.
| 【1】 Ueda, E.; Yoshikawa, Y.; Ishino, Y.; Sakurai, H.; Kojima, Y.; Potential insulinominetic agents of zinc(II) complexes with picolinamide derivatives: Preparations of complexes, in vitro and in vivo studies. Chem Pharm Bull 2002, 50, 3, 337. |