diethyl 2-[[4-(2-propynylamino)benzoyl]amino]pentanedioate -Drug Synthesis Database

【结构式】

【分子编号】34312

【品名】diethyl 2-[[4-(2-propynylamino)benzoyl]amino]pentanedioate

【CA登记号】

【分子式】C₁₉H₂₄N₂O₅

【分子量】360.41004

【元素组成】C 63.32% H 6.71% N 7.77% O 22.2%

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：(IV)

The alkylation of diethyl N-(4-aminobenzoyl)glutamate (I) with propargyl bromide (II) in hot ethanol gives diethyl N-[4-(propargylamino)benzoyl]glutamate (III), which is condensed with 2-amino-6-bromomethyl-4-hydroxyquinazoline (IV) by means of triethylamine in hot 2-ethoxyethanol (or CaCO3 in dimethylacetamide) yielding diethyl N-[4-[N-[(2-amino-4-hydroxy-6-quinazolinyl)methyl]prop-2-ynylamino]benzoyl]-L-glutamate (V). Finally, this compound is saponified with NaOH in ethanol-water.

参考文献中间体

合成目标

【1】 Jones, T.R.; Harrap, K.R.; Calvert, A.H.; Anti-cancer quinazoline derivatives. EP 0031237; GB 2065653; US 4447608; US 4564616 .
【2】 Hopkins, S.J.; Serradell, M.N.; Castaner, J.; CB-3717. Drugs Fut 1984, 9, 12, 893.

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)	25036	Diethyl N-(4-aminobenzoyl)glutamate; diethyl 2-[(4-aminobenzoyl)amino]pentanedioate		C₁₆H₂₂N₂O₅	详情	详情
(II)	11176	3-Bromopropyne; 3-Bromo-1-propyne	106-96-7	C₃H₃Br	详情	详情
(III)	34311	ethyl (2S)-1-[(2R)-2-methyl-3-sulfanylpropanoyl]-2,3-dihydro-1H-indole-2-carboxylate		C₁₅H₁₉NO₃S	详情	详情
(IV)	34312	diethyl 2-[[4-(2-propynylamino)benzoyl]amino]pentanedioate		C₁₉H₂₄N₂O₅	详情	详情
(V)	34313	2-amino-6-(bromomethyl)-4-quinazolinol		C₉H₈BrN₃O	详情	详情

Extended Information