ethyl 3-isocyanatobenzoate -Drug Synthesis Database

【结构式】

【分子编号】18996

【品名】ethyl 3-isocyanatobenzoate

【CA登记号】67531-68-4

【分子式】C₁₀H₉NO₃

【分子量】191.1864

【元素组成】C 62.82% H 4.74% N 7.33% O 25.11%

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：(VII)

N-Phenyl-1,2-phenylenediamine (I) was alkylated with bromoacetanilide (II) in the presence of potassium carbonate in DMF, and the resulting alkylated phenylenediamine (III) was condensed with diacid chloride (IV) in THF to afford dioxobenzodiazepine (V). Reduction of the hydrazone function with zinc-acetic acid provided amine (VI) (1). Urea (VIII) was then prepared by treatment of amine (VI) with isocyanate (VII) in dichloromethane, and finally, ethyl ester was hydrolyzed on treatment with K2CO3 in a refluxing mixture of methanol and THF.

参考文献中间体

合成目标

【1】 Hirst, G.C.; et al.; Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity (II): Optimization of the C3 amino substituent. J Med Chem 1996, 39, 26, 5236.
【2】 Finch, H.; Shah, P.; Carr, R.A.E. (Glaxo Wellcome plc); 1,5-Benzodiazepine derivs. having CCK and/or gastrin antagonistic activity. US 5585376; US 5646140; WO 9424149; WO 9424151 .

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)	18990	N-(2-aminophenyl)-N-phenylamine; N(1)-phenyl-1,2-benzenediamine	534-85-0	C₁₂H₁₂N₂	详情	详情
(II)	18991	2-bromo-N-isopropyl-N-phenylacetamide		C₁₁H₁₄BrNO	详情	详情
(III)	18992	2-(2-anilinoanilino)-N-isopropyl-N-phenylacetamide		C₂₃H₂₅N₃O	详情	详情
(IV)	17971	2-(2-phenylhydrazono)malonoyl dichloride		C₉H₆Cl₂N₂O₂	详情	详情
(V)	18994	2-[2,4-dioxo-5-phenyl-3-[(Z)-2-phenylhydrazono]-4,5-dihydro-1H-1,5-benzodiazepin-1(2H)-yl]-N-isopropyl-N-phenylacetamide		C₃₂H₂₉N₅O₃	详情	详情
(VI)	18995	2-(3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)-N-isopropyl-N-phenylacetamide		C₂₆H₂₆N₄O₃	详情	详情
(VII)	18996	ethyl 3-isocyanatobenzoate	67531-68-4	C₁₀H₉NO₃	详情	详情
(VIII)	18997	ethyl 3-[[([1-[2-(isopropylanilino)-2-oxoethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]amino)carbonyl]amino]benzoate		C₃₆H₃₅N₅O₆	详情	详情

Extended Information