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【结 构 式】 
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【分子编号】42069 【品名】5-(chloromethyl)imidazo[1,2-a]pyridine 【CA登记号】 |
【 分 子 式 】C8H7ClN2 【 分 子 量 】166.60976 【元素组成】C 57.67% H 4.23% Cl 21.28% N 16.81% |
合成路线1
该中间体在本合成路线中的序号：(II)The chlorination of 5-(hydroxymethyl)imidazo[1,2-a]pyridine (I) with SOCl2 in dichloromethane gives the corresponding chloromethyl derivative (II), which is condensed with 1,4-diaminobutane (III) in refluxing acetonitrile to yield 5-(4-aminobutylaminomethyl)imidazo[1,2-a]pyridine (IV). The sulfonation of (IV) with N-phenyltrifluoromethylsulfonimide (V) and TEA in acetonitrile affords the sulfonamide (VI), which is protected with Boc2O in ethanol to provide the carbamate (VII). The acylation of (VII) with trichloroacetyl chloride and DMAP in refluxing chloroform gives the 3-trichloroacetyl derivative (VIII), which is finally cyclized by means of Tms-I and NaHCO3 in chloroform.
| 【1】 Ikemoto, T.; et al.; A practical synthesis of the chronic renal disease agent, 4,5-dihydro-3H-1,4,8b-triazaacenaphthylen-3-one derivatives, using regioselective chlorination of ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxy with N-chlorosuccinimide. Tetrahedron 2000, 56, 40, 7915. |
| 【2】 Takatani, M.; Shibouta, Y.; Tomimatsu, K.; Kawamoto, T. (Takeda Chemical Industries, Ltd.); Tricyclic cpds., their production and use. EP 0771319; JP 1996081467; WO 9602542 . |
| 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) | 42068 | imidazo[1,2-a]pyridin-5-ylmethanol | C8H8N2O | 详情 | 详情 | |
| (II) | 42069 | 5-(chloromethyl)imidazo[1,2-a]pyridine | C8H7ClN2 | 详情 | 详情 | |
| (III) | 42070 | 1,4-butanediamine; 4-aminobutylamine | 110-60-1 | C4H12N2 | 详情 | 详情 |
| (IV) | 42071 | N(1)-(imidazo[1,2-a]pyridin-5-ylmethyl)-1,4-butanediamine; N-(4-aminobutyl)-N-(imidazo[1,2-a]pyridin-5-ylmethyl)amine | C12H18N4 | 详情 | 详情 | |
| (V) | 17573 | N-Phenyltrifluoromethanesulfonimide; Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide | 37595-74-7 | C8H5F6NO4S2 | 详情 | 详情 |
| (VI) | 42072 | trifluoro-N-[4-[(imidazo[1,2-a]pyridin-5-ylmethyl)amino]butyl]methanesulfonamide | C13H17F3N4O2S | 详情 | 详情 | |
| (VII) | 42073 | tert-butyl imidazo[1,2-a]pyridin-5-ylmethyl(4-[[(trifluoromethyl)sulfonyl]amino]butyl)carbamate | C18H25F3N4O4S | 详情 | 详情 | |
| (VIII) | 42074 | tert-butyl [3-(2,2,2-trichloroacetyl)imidazo[1,2-a]pyridin-5-yl]methyl(4-[[(trifluoromethyl)sulfonyl]amino]butyl)carbamate | C20H24Cl3F3N4O5S | 详情 | 详情 |