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【结 构 式】

【分子编号】50088

【品名】5-(azidomethyl)-N-(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyridinyl)-3-(4-chloro-3-nitrophenyl)-4,5-dihydro-5-isoxazolecarboxamide

【CA登记号】

【 分 子 式 】C26H25ClN8O6S

【 分 子 量 】613.05352

【元素组成】C 50.94% H 4.11% Cl 5.78% N 18.28% O 15.66% S 5.23%

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:(VIII)

Conversion of the bromo derivative (I) into the corresponding azido compound (II) is performed by treatment with NaN3 in DMSO. Separately, aldehyde (III) is treated with hydroxylamine to provide oxime (IV), which is then condensed with derivative (II) by means of bleach in CH2Cl2 to furnish isoxazoline derivative (V). Hydrolysis of the methyl ester of (V) by means of LiOH in THF affords carboxylic acid (VI), which is treated with SOCl2 and then condensed with amine (VII) by means of Et3N to give carboxamide (VIII). Reduction of the azido moiety of (VIII) by means of P(OEt)3 in THF yields amine (IX), which is then derivatized by reaction with mesyl chloride (MeSO2Cl) to provide mesylate (X). Finally, the desired compound is obtained by treatment of (X) with TFA for tert-butyl group removal, followed by reduction of the nitro moiety with SnCl2.

1 Wong, P.C.; Ellis, C.D.; Rossi, K.A.; Wexler, R.R.; Wright, M.R.; Quan, M.L.; Lam, P.Y.; He, M.Y.; Knabb, R.M.; Liauw, A.Y.; Nonbenzamidine isoxazolin derivatives as factor Xa inhibitors. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 52.
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) 32407 methyl 2-(bromomethyl)acrylate C5H7BrO2 详情 详情
(II) 50083 methyl 2-(azidomethyl)acrylate C5H7N3O2 详情 详情
(III) 50084 3-Nitro-4-chlorobenzaldehyde; 4-Chloro-3-nitrobenzaldehyde 16588-34-4 C7H4ClNO3 详情 详情
(IV) 50085 N-(4-chloro-3-nitrobenzyl)hydroxylamine; 1-chloro-4-[(hydroxyamino)methyl]-2-nitrobenzene C7H7ClN2O3 详情 详情
(V) 50086 methyl 5-(azidomethyl)-3-(4-chloro-3-nitrophenyl)-4,5-dihydro-5-isoxazolecarboxylate C12H10ClN5O5 详情 详情
(VI) 50087 5-(azidomethyl)-3-(4-chloro-3-nitrophenyl)-4,5-dihydro-5-isoxazolecarboxylic acid C11H8ClN5O5 详情 详情
(VII) 32412 2-(6-amino-3-pyridinyl)-N-(tert-butyl)benzenesulfonamide C15H19N3O2S 详情 详情
(VIII) 50088 5-(azidomethyl)-N-(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyridinyl)-3-(4-chloro-3-nitrophenyl)-4,5-dihydro-5-isoxazolecarboxamide C26H25ClN8O6S 详情 详情
(IX) 50089 5-(aminomethyl)-N-(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyridinyl)-3-(4-chloro-3-nitrophenyl)-4,5-dihydro-5-isoxazolecarboxamide C26H27ClN6O6S 详情 详情
(X) 50090 N-(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyridinyl)-3-(4-chloro-3-nitrophenyl)-5-[[(methylsulfonyl)amino]methyl]-4,5-dihydro-5-isoxazolecarboxamide C27H29ClN6O8S2 详情 详情
Extended Information