N-[2-(3-[4-[(2,2-dimethylpropanoyl)amino]phenyl]-3-oxopropanoyl)-3-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2,2-dimethylpropanamide -Drug Synthesis Database

【结构式】

【分子编号】36666

【品名】N-[2-(3-[4-[(2,2-dimethylpropanoyl)amino]phenyl]-3-oxopropanoyl)-3-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2,2-dimethylpropanamide

【CA登记号】

【分子式】C₃₀H₃₈N₂O₆

【分子量】522.6416

【元素组成】C 68.94% H 7.33% N 5.36% O 18.37%

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：(V)

The reaction of 3-aminophenol (I) with pivaloyl chloride and then with DHP and TsOH gives the protected pivalanilide (II), which is condensed with ethyl chloroformate by means of BuLi in THF yielding the benzoate ester (III). The condensation of benzoate (III) with acetophenone (IV) by means of NaH in refluxing dioxane affords the intermediate diketone (V), which, without purification, was treated with HCl in ethanol at room temperature to give the protected flavone (VI). Finally, thee removal of the two pivaloyl protecting groups was effected with HCl in refluxing ethanol.

参考文献中间体

合成目标

【1】 Akama, T.; et al.; Novel 5-aminoflavone derivatives as specific antitumor agents in breast cancer. J Med Chem 1996, 39, 18, 3461.
【2】 Shida, Y.; Sagaya, T.; Gomi, K.; Kasai, M.; Morimoto, M. (Kyowa Hakko Kogyo Co., Ltd.); 5-Aminoflavone derivs.. EP 0374789; JP 1990256673 .
【3】 Sugaya, T.; et al.; Synthesis of a 6H-pyrazolo[4,5,1-de]acridin-6-one derivative: A useful intermediate of antitumor agents. Synthesis 1994, 73.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	13597	2,2-Dimethylpropanoyl chloride; Pivaloyl chloride	3282-30-2	C₅H₉ClO	详情	详情
(I)	23766	3-aminophenol	591-27-5	C₆H₇NO	详情	详情
(II)	36663	2,2-dimethyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)phenyl]propanamide		C₁₆H₂₃NO₃	详情	详情
(III)	36664	ethyl 2-[(2,2-dimethylpropanoyl)(ethoxycarbonyl)amino]-6-(tetrahydro-2H-pyran-2-yloxy)benzoate		C₂₂H₃₁NO₇	详情	详情
(IV)	36665	N-(4-acetylphenyl)-2,2-dimethylpropanamide		C₁₃H₁₇NO₂	详情	详情
(V)	36666	N-[2-(3-[4-[(2,2-dimethylpropanoyl)amino]phenyl]-3-oxopropanoyl)-3-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2,2-dimethylpropanamide		C₃₀H₃₈N₂O₆	详情	详情
(VI)	36667	N-(4-[5-[(2,2-dimethylpropanoyl)amino]-4-oxo-4H-chromen-2-yl]phenyl)-2,2-dimethylpropanamide		C₂₅H₂₈N₂O₄	详情	详情

Extended Information