2-[[4-(2-benzoyl-4-chlorophenyl)-4H-1,2,4-triazol-3-yl]methyl]-1H-isoindole-1,3(2H)-dione -Drug Synthesis Database

【结构式】

【分子编号】35945

【品名】2-[[4-(2-benzoyl-4-chlorophenyl)-4H-1,2,4-triazol-3-yl]methyl]-1H-isoindole-1,3(2H)-dione

【CA登记号】

【分子式】C₂₄H₁₅ClN₄O₃

【分子量】442.86096

【元素组成】C 65.09% H 3.41% Cl 8.01% N 12.65% O 10.84%

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：(XVII)

The reaction of (III) with (XI) by means of pyridine in THF gives 1,3-dioxo-2-isoindolineacetic acid [[N-(2-benzoyl-4-chlorophenyl)-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide (XVI), which by cyclization by means of trifluoroacetic acid in refluxing toluene yields 5-chloro-2-[3-(phtalimidomethyl)-4H-1,2,4-triazol-4-yl-benzophenone (XVII). The reaction of (XVII) with N,N,N',N'-tetramethyldiaminomethane (A) by means of acetyl chloride in DMF affords 5-chloro-2-[3-[(dimethylamino)methyl-5-(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benzophenone (XVIII), which is finally cyclized by means of hydrazine in hot ethanol.

参考文献中间体

合成目标

【1】 Gall, M.; Hester, J.B.; US 3957761 .
【2】 Castaner, J.; Pento, J.T.; Blancafort, P.; Serradell, M.N.; Adinazolam. Drugs Fut 1983, 8, 2, 87.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	14349	N,N,N,N-tetramethylmethanediamine; tetramethylmethylenediamine;bis(dimethylamino)methane; N-[(dimethylamino)methyl]-N,N-dimethylamine	51-80-9	C₅H₁₄N₂	详情	详情
(III)	35937	3-amino-6-chloro-4-phenyl-3,4-dihydro-4-quinazolinol		C₁₄H₁₂ClN₃O	详情	详情
(XI)	10278	2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride	6780-38-7	C₁₀H₆ClNO₃	详情	详情
(XVI)	35944	N-(2-benzoyl-4-chlorophenyl)-N,N'-bis[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]hydrazonoformamide		C₃₄H₂₂ClN₅O₇	详情	详情
(XVII)	35945	2-[[4-(2-benzoyl-4-chlorophenyl)-4H-1,2,4-triazol-3-yl]methyl]-1H-isoindole-1,3(2H)-dione		C₂₄H₁₅ClN₄O₃	详情	详情
(XVIII)	35946	2-([4-(2-benzoyl-4-chlorophenyl)-5-[(dimethylamino)methyl]-4H-1,2,4-triazol-3-yl]methyl)-1H-isoindole-1,3(2H)-dione		C₂₇H₂₂ClN₅O₃	详情	详情

Extended Information