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【结 构 式】

【分子编号】26597

【品名】tert-butyl 2-[5-(azidomethyl)-4-methyl-1H-imidazol-1-yl]acetate

【CA登记号】

【 分 子 式 】C11H17N5O2

【 分 子 量 】251.28848

【元素组成】C 52.58% H 6.82% N 27.87% O 12.73%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The condensation of 5-(hydroxymethyl)-4-methyl-1H-imidazole (I) with tert-butyl bromoacetate (II) by means of K2CO3 in DMF gives the imidazolylacetic ester (III), which is treated with diphenylphosphoryl azide and DBU in DMF yielding the azidomethyl compound (IV). The reduction of (IV) with H2 over Pd/C in ethyl acetate affords the aminomethyl compound (V), which is acylated with 2-[3-(benzylsulfonamido)-6-methyl-2-oxo-1,2-dihydropyridin-1-yl]acetic acid (VI) by means of EDC and HOBT in DMF providing the carboxamide (VII). Elimination of the tert-butyl group of (VII) with HCl in ethyl acetate gives the free carboxylic acid (VIII), which is finally amidated with tert-butylamine by means of EDC and HOBT in DMF.

1 Naylor-Olsen, A.M.; Newton, C.L.; Isaacs, R.C.A.; Dorsey, B.D. (Merck & Co., Inc.); Thrombin inhibitors. EP 0969840; US 5932606; WO 9842342 .
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) 26595 (4-methyl-1H-imidazol-5-yl)methanol 38585-62-5 C5H8N2O 详情 详情
(II) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(III) 26596 tert-butyl 2-[5-(hydroxymethyl)-4-methyl-1H-imidazol-1-yl]acetate C11H18N2O3 详情 详情
(IV) 26597 tert-butyl 2-[5-(azidomethyl)-4-methyl-1H-imidazol-1-yl]acetate C11H17N5O2 详情 详情
(V) 26598 tert-butyl 2-[5-(aminomethyl)-4-methyl-1H-imidazol-1-yl]acetate C11H19N3O2 详情 详情
(VI) 26599 2-[3-[(benzylsulfonyl)amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid C15H16N2O5S 详情 详情
(VII) 26600 tert-butyl 2-[5-[([2-[3-[(benzylsulfonyl)amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetyl]amino)methyl]-4-methyl-1H-imidazol-1-yl]acetate C26H33N5O6S 详情 详情
(VIII) 26601 2-[5-[([2-[3-[(benzylsulfonyl)amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetyl]amino)methyl]-4-methyl-1H-imidazol-1-yl]acetic acid C22H25N5O6S 详情 详情
Extended Information