2-bromo-1-(2,4,6-triisopropylphenyl)-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】14889

【品名】2-bromo-1-(2,4,6-triisopropylphenyl)-1-ethanone

【CA登记号】

【分子式】C₁₇H₂₅BrO

【分子量】325.2889

【元素组成】C 62.77% H 7.75% Br 24.56% O 4.92%

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：(IX)

SR 27417 (N-(2-dimethylaminoethyl)-N-(3-pyridinylmethyl)[4-(2,4,6-triisopropylphenyl)thiazol-2-yl]amine difumarate) was prepared via a convergent route. Reductive amination of N,N-dimethylaminoethanamine (I) and pyridyl-3-carboxaldehyde (II) by sodium borohydride gave the amine (III). Eaction of pivaloyl chloride (IV) and potassium thiocyanate in anhydrous acetone provided the pivaloyl isothiocyanate (V), which was condensed in situ with the amine (III) to afford the protected thiourea (VI). Chlorhydric hydrolysis of (IV) gave the thiourea (VII) with the bromoketene (IX) in refluxing ethanol led to SR 27417.

参考文献中间体

合成目标

【1】 Herbert, J.M.; Valette, G.; Bernat, A.; Savi, P.; Maffrand, J.P.; Le Fur, G.; SR 27417, a highly potent, selective and long-acting antagonist of the PAF receptor. Drugs Fut 1992, 17, 11, 1011.

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)	14881	N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine	108-00-9	C₄H₁₂N₂	详情	详情
(II)	12849	Nicotinaldehyde; 3-Pyridinecarboxaldehyde	500-22-1	C₆H₅NO	详情	详情
(III)	14883	N-[2-(dimethylamino)ethyl]-N-(3-pyridinylmethyl)amine; N(1),N(1)-dimethyl-N(2)-(3-pyridinylmethyl)-1,2-ethanediamine		C₁₀H₁₇N₃	详情	详情
(IV)	13597	2,2-Dimethylpropanoyl chloride; Pivaloyl chloride	3282-30-2	C₅H₉ClO	详情	详情
(V)	14885	2,2-dimethylpropanoyl isothiocyanate		C₆H₉NOS	详情	详情
(VI)	14886	N-[2-(dimethylamino)ethyl]-N'-(2,2-dimethylpropanoyl)-N-(3-pyridinylmethyl)thiourea		C₁₆H₂₆N₄OS	详情	详情
(VII)	14887	N-[2-(dimethylamino)ethyl]-N-(3-pyridinylmethyl)thiourea		C₁₁H₁₈N₄S	详情	详情
(VIII)	14888	1,3,5-triisopropylbenzene	717-74-8	C₁₅H₂₄	详情	详情
(IX)	14889	2-bromo-1-(2,4,6-triisopropylphenyl)-1-ethanone		C₁₇H₂₅BrO	详情	详情

Extended Information