2-azido-1-phenyl-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】26720

【品名】2-azido-1-phenyl-1-ethanone

【CA登记号】

【分子式】C₈H₇N₃O

【分子量】161.1632

【元素组成】C 59.62% H 4.38% N 26.07% O 9.93%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XI)

The intermediate sulfonyl chloride (VIII) has been obtained as follows: The reaction of phenacyl bromide (X) with sodium azide in hot DMF gives the azide (XI), which is condensed with 3-cyclopentylpropionyl chloride (XII) by means of LDA yielding the enol ester (XIII). The cyclization of (XIII) by means of triethyl phosphite in refluxing hexane affords 2-(2-cyclopentylethyl)-5-phenyloxazole (XIV), which is finally sulfonated with chlorosulfonic acid to afford the target sulfonyl chloride (VIII).

参考文献中间体

合成目标

【1】 Ok, H.O.; Candelore, M.R.; Reigle, L.B.; et al.; Substituted oxazole benzenesulfonamides as potent human beta3 adrenergic receptor agonists. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 114.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	26718	4-[2-(2-cyclopentylethyl)-1,3-oxazol-5-yl]benzenesulfonyl chloride		C₁₆H₁₈ClNO₃S	详情	详情
(X)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(XI)	26720	2-azido-1-phenyl-1-ethanone		C₈H₇N₃O	详情	详情
(XII)	26721	3-cyclopentylpropanoyl chloride	104-97-2	C₈H₁₃ClO	详情	详情
(XIII)	26722	(Z)-2-azido-1-phenylethenyl 3-cyclopentylpropanoate		C₁₆H₁₉N₃O₂	详情	详情
(XIV)	26723	2-(2-cyclopentylethyl)-5-phenyl-1,3-oxazole		C₁₆H₁₉NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Treatment of 6-aminoisoquinoline (I) with 1,1'-thiocarbonyldi-2(1H)-pyridone (II) provides the isothiocyanate (III). Subsequent condensation of (III) with 2-azidoacetophenone (IV) in the presence of triphenylphosphine affords the title oxazole derivative.

参考文献中间体

合成目标

【1】 Chen, P.; Norris, D.; Haslow, K.D.; Dhar, T.G.M.; Pitts, W.J.; Watterson, S.H.; Cheney, D.L.; Bassolino, D.A.; Fleener, C.A.; Rouleau, K.A.; Hollenbaugh, D.L.; Townsend, R.M.; Barrish, J.C.; Iwanowicz, E.J.; Identification of novel and potent isoquinoline aminooxazole-based IMPDH inhibitors. Bioorg Med Chem Lett 2003, 13, 7, 1345.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	64245	6-isoquinolinamine; 6-isoquinolinylamine	C₉H₈N₂	详情	详情
(II)	61696	1-{[2-oxo-1(2H)-pyridinyl]carbothioyl}-2(1H)-pyridinone	C₁₁H₈N₂O₂S	详情	详情
(III)	64246	6-isothiocyanatoisoquinoline; 6-isoquinolinyl isothiocyanate	C₁₀H₆N₂S	详情	详情
(IV)	26720	2-azido-1-phenyl-1-ethanone	C₈H₇N₃O	详情	详情

Extended Information