1,2,3-Benzotriazole; 1H-Benzotriazole; Azimidobenzene; Benzotriazol -Drug Synthesis Database

【结构式】

【分子编号】57599

【品名】1,2,3-Benzotriazole; 1H-Benzotriazole; Azimidobenzene; Benzotriazol

【CA登记号】95-14-7

【分子式】C₆H₅N₃

【分子量】119.12592

【元素组成】C 60.5% H 4.23% N 35.27%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

Reaction of 3,5-dichlorobenzamide (V) with pivalaldehyde (VI) in the presence of benzotriazole (VII) gives rise to the benzotriazolyl benzamide (VIII). This is then condensed with the diamino cyclobutene (IV) to afford the racemic adduct (IX), which is finally resolved into the enantiomers employing chiral chromatography.

参考文献中间体

合成目标

【1】 Kort, M.E.; Gregg, R.J.; Perez-Medrano, A.; et al.; Aminal-containing ATP-sensitive potassium channel openers for the treatment of bladder overactivity. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 351.
【2】 Basha, F.Z.; Carroll, W.A.; Kort, M.E.; Gregg, R.J.; Dinges, J.; Perez Medrano, A. (Abbott Laboratories Inc.); Aminal diones as potassium channel openers. US 2002165264; US 6495576; WO 0262761 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	57597	3-amino-4-[(2-chloro-3-pyridinyl)amino]-3-cyclobutene-1,2-dione		C₉H₆ClN₃O₂	详情	详情
(V)	57598	2-Amino-3,5-dichlorobenzoic acid; 3,5-Dichloroanthranilic acid	5980-23-4	C₇H₅Cl₂NO	详情	详情
(VI)	19797	Trimethylacetaldehyde; pivalaldehyde; 2,2-Dimethylpropionaldehyde; 2,2-Dimethylpropanal	630-19-3	C₅H₁₀O	详情	详情
(VII)	57599	1,2,3-Benzotriazole; 1H-Benzotriazole; Azimidobenzene; Benzotriazol	95-14-7	C₆H₅N₃	详情	详情
(VIII)	57600	N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl]-3,5-dichlorobenzamide		C₁₈H₁₈Cl₂N₄O	详情	详情
(IX)	57601	3,5-dichloro-N-[1-({2-[(2-chloro-3-pyridinyl)amino]-3,4-dioxo-1-cyclobuten-1-yl}amino)-2,2-dimethylpropyl]benzamide		C₂₁H₁₉Cl₃N₄O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIII)

Alkylation of benzotriazole (XIII) with chloroacetonitrile leads to a mixture of regioisomeric cyanomethyl derivatives (XIV) and (XV). The minor isomer (XV) is then condensed with aldehyde (XII) employing ethanolic KF to produce the substituted acrylonitrile (XVI). Finally, the acetamide function of (XVI) is converted into the target thioamide by treatment with Lawesson's reagent

参考文献中间体

合成目标

【1】 Das, J.; et al.; Geometrical and regioisomeric effects on biological activity of some novel stilbene-type oxazolidinones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1325.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIII)	57599	1,2,3-Benzotriazole; 1H-Benzotriazole; Azimidobenzene; Benzotriazol	95-14-7	C₆H₅N₃	详情	详情
(XIV)	61810	2-(1H-1,2,3-benzotriazol-1-yl)acetonitrile; BENZOTRIAZOL-1-YL-ACETONITRILE; 1H-BENZOTRIAZOLE-1-ACETONITRILE		C₈H₆N₄	详情	详情
(XV)	61811	2-(2H-1,2,3-benzotriazol-2-yl)acetonitrile		C₈H₆N₄	详情	详情
(XVI)	61812	N-{[(5S)-3-(4-formylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide		C₁₃H₁₄N₂O₄	详情	详情
(XVII)	61813	N-[((5S)-3-{4-[(E)-2-(2H-1,2,3-benzotriazol-2-yl)-3-nitrilo-1-propenyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide		C₂₁H₁₈N₆O₃	详情	详情

Extended Information