N-(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyridinyl)-3-(3-cyanophenyl)-5-(1H-1,2,3,4-tetraazol-1-ylmethyl)-4,5-dihydro-5-isoxazolecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】32413

【品名】N-(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyridinyl)-3-(3-cyanophenyl)-5-(1H-1,2,3,4-tetraazol-1-ylmethyl)-4,5-dihydro-5-isoxazolecarboxamide

【CA登记号】

【分子式】C₂₈H₂₇N₉O₄S

【分子量】585.64664

【元素组成】C 57.43% H 4.65% N 21.53% O 10.93% S 5.48%

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)

The condensation of 2-(bromomethyl)acrylic acid methyl ester (I) with 1H-tetrazole (II) by means of K2CO3 in DMF gives 2-(1-tetrazolylmethyl)acrylic acid methyl ester (III), which is cyclized with 3-cyanobenzaldehyde oxime (IV) by means of NaOCl yielding the oxazoline carboxylic ester (V). The hydrolysis of (V) with LiOH in THF affords the free carboxylic acid (VI), which is condensed with 2-(6-aminopyridin-3-yl)-N-tert-butybenzenesulfonamide (VII) by means of SOCl2 and triethylamine giving the carboxamide (VIII). Finally, this compound is treated with HCl and then with ammonium acetate to eliminate the tert-butyl protecting group and to hydrolyze the cyano group to the target amidino compound.

参考文献中间体

合成目标

【1】 Alexander, R.S.; Wesler, R.R.; Ellis, C.D.; Quan, M.L.; Liauw, A.Y.; Wong, P.C.; Lam, G.; Knabb, R.M.; Wright, M.R.; Design and synthesis of isoxazoline derivatives as factor Xa inhibitors. 2(1). J Med Chem 1999, 42, 15, 2760.

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)	32408	1H-1,2,3,4-tetraazole; Tetrazole	288-94-8	CH₂N₄	详情	详情
(III)	32409	methyl 2-(1H-1,2,3,4-tetraazol-1-ylmethyl)acrylate		C₆H₈N₄O₂	详情	详情
(IV)	23357	3-[(hydroxyimino)methyl]benzonitrile		C₈H₆N₂O	详情	详情
(V)	32410	methyl 3-(3-cyanophenyl)-5-(1H-1,2,3,4-tetraazol-1-ylmethyl)-4,5-dihydro-5-isoxazolecarboxylate		C₁₄H₁₂N₆O₃	详情	详情
(VI)	32411	3-(3-cyanophenyl)-5-(1H-1,2,3,4-tetraazol-1-ylmethyl)-4,5-dihydro-5-isoxazolecarboxylic acid		C₁₃H₁₀N₆O₃	详情	详情
(VII)	32412	2-(6-amino-3-pyridinyl)-N-(tert-butyl)benzenesulfonamide		C₁₅H₁₉N₃O₂S	详情	详情
(VIII)	32413	N-(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyridinyl)-3-(3-cyanophenyl)-5-(1H-1,2,3,4-tetraazol-1-ylmethyl)-4,5-dihydro-5-isoxazolecarboxamide		C₂₈H₂₇N₉O₄S	详情	详情

Extended Information