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【结 构 式】

【药物名称】

【化学名称】4(S)-(Cyclopropylethynyl)-6-methoxy-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

【CA登记号】205754-67-2 (undefined isomer)

【 分 子 式 】C15H12F3NO3

【 分 子 量 】311.26299

【开发单位】Bristol-Myers Squibb (Originator)

【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Reverse Transcriptase Inhibitors

合成路线1

The acylation of 4-methoxyaniline (I) with pivaloyl chloride (II) and TEA in CH2Cl2 gives the anilide (III), which is condensed with ethyl trifluoroacetate (IV) by means of n-BuLi in THF yielding the trifluoroacetyl derivative (V). The hydrolysis of the amido group of (V) with 6N HCl in refluxing DMF affords the 2-aminoacetophenone (VI), which is condensed with cyclopropylacetylene (VII) by means of n-BuLi in THF to give the tertiary alcohol (VIII). Finally, this compound is cyclized with phosgene and DIPEA in toluene yielding the racemic form of target compound.

1 Ko, S.S.; Patel, M.; Cordova, B.C.; Klabe, R.M.; Srivastava, A.S.; Markwalder, J.A.; McHugh, R.J. Jr.; Seitz, S.P.; Trainor, G.L.; Erickson-Vittanen, S.; Synthesis and evaluation of analogs of efavirenz (Sustiva(TM)) as HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem Lett 1999, 9, 19, 2805.
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) 10478 p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine 104-94-9 C7H9NO 详情 详情
(II) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(III) 40412 N-(4-methoxyphenyl)-2,2-dimethylpropanamide C12H17NO2 详情 详情
(IV) 14588 Ethyl 2,2,2-trifluoroacetate; Trifluoroethyl acetate 383-63-1 C4H5F3O2 详情 详情
(V) 40413 N-[4-methoxy-2-(2,2,2-trifluoroacetyl)phenyl]-2,2-dimethylpropanamide C14H16F3NO3 详情 详情
(VI) 40414 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro-1-ethanone C9H8F3NO2 详情 详情
(VII) 16575 1-ethynylcyclopropane; cyclopropyl acetylene 6746-94-7 C5H6 详情 详情
(VIII) 40415 2-(2-amino-5-methoxyphenyl)-4-cyclopropyl-1,1,1-trifluoro-3-butyn-2-ol C14H14F3NO2 详情 详情
Extended Information