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【结 构 式】

【分子编号】52208

【品名】N-(2-aminoethyl)-2-bromo-N-{[1-(4-pyridinyl)-4-piperidinyl]methyl}acetamide

【CA登记号】

【 分 子 式 】C15H23BrN4O

【 分 子 量 】355.27798

【元素组成】C 50.71% H 6.53% Br 22.49% N 15.77% O 4.5%

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:(IX)

The condensation of 4-piperidinylmethanol (I) with 4-chloropyridine (II) gives 1-(4-pyridyl)piperidin-4-ylmethanol (III), which is oxidized with (COCl)2 and TEA in DMSO to yield the carbaldehyde (IV). The reductocondensation of (IV) with N-(tert-butoxycarbonyl)ethylene-1,2-diamine (V) by means of sodium triacetoxyborohydride and acetic acid affords the corresponding adduct as the borane complex (VI), which is acylated with bromoacetyl chloride (VII) and TEA in dichloromethane, providing the bromoacetamide (VIII). The cleavage of the boron complex and the Boc protecting group of (VIII) with TFA and anisole in ethyl ether gives the precursor (IX), which is cyclized to the piperazinone (X) by means of TEA in DMF. Finally, compound (X) is condensed with 6-chloronaphthalene-2-sulfonyl chloride by means of TEA in dichloromethane to yield the target sulfonamide.

1 Nishida, H.; et al.; Synthesis and evaluation of 1-arylsulfonyl-3-piperazinone derivatives as factor Xa inhibitor. Chem Pharm Bull 2001, 49, 10, 1237.
2 Miyazaki, Y.; Mukaihira, T.; Nishida, H.; Hosaka, Y.; Matsusue, T. (Mochida Pharmaceutical Co., Ltd.); Aromatic cpds. having cyclic amino or salts thereof. EP 1048652; WO 9933805 .
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) 32954 4-piperidinylmethanol C6H13NO 详情 详情
(II) 32889 4-chloropyridine 7379-35-3 C5H4ClN 详情 详情
(III) 45860 [1-(4-pyridinyl)-4-piperidinyl]methanol C11H16N2O 详情 详情
(IV) 52205 1-(4-pyridinyl)-4-piperidinecarbaldehyde C11H14N2O 详情 详情
(V) 13241 N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate;tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate 57260-73-8 C7H16N2O2 详情 详情
(VI) 52206   C22H37BN4O7 详情 详情
(VII) 27903 2-Bromoacetyl chloride 22118-09-8 C2H2BrClO 详情 详情
(VIII) 52207   C24H38BBrN4O8 详情 详情
(IX) 52208 N-(2-aminoethyl)-2-bromo-N-{[1-(4-pyridinyl)-4-piperidinyl]methyl}acetamide C15H23BrN4O 详情 详情
(X) 52209 1-{[1-(4-pyridinyl)-4-piperidinyl]methyl}-2-piperazinone C15H22N4O 详情 详情
(XI) 45865 6-chloro-2-naphthalenesulfonyl chloride C10H6Cl2O2S 详情 详情
Extended Information