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【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

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).

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.

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 CAS号 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