• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】14722

【品名】1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetraazol-1-yl)ethyl]-3-methyltetrahydro-4(1H)-pyridinone

【CA登记号】

【 分 子 式 】C11H19N5O2

【 分 子 量 】253.30436

【元素组成】C 52.16% H 7.56% N 27.65% O 12.63%

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:(IV)

The synthesis of tritium-labeled brifentanil has been described: The hydrogenolysis of 1-benzyl-3-methylpiperidin-4-one (I) with H2 over Pd/C in ethanol gives the free piperidone (II), which is condensed with 1-(2-bromoethyl)-4-ethyl-4,5-dihydro-1H-tetrazol-5-one (III) by means of NaI and Na2CO3 in acetonitrile, yielding the condensation product (IV). The reductocondensation of (IV) with 4-bromo-2-fluoroaniline by means of NaBH3CN and HCl in methanol affords the substituted aniline (VI), which is acylated with 2-methoxyacetyl chloride (VII) and submitted to chromatographic (HPLC) separation to obtain the cis-isomer of bromobrifentanil (VIII). Finally, this compound is submitted to debromination with tritium gas and Pd/C in ethanol to afford [3H]-brifentanil.

1 Nugent, R.P.; Huang, B.S.; Filer, C.N.; The synthesis of [fluorophenyl-H-3(N)]ocfentanil and [fluorophenyl-H-3(N)]brifentanil. J Label Compd Radiopharm 1995, 36, 11, 1019.
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) 14714 1-Benzyl-3-methyl-4-piperidone; 1-benzyl-3-methyltetrahydro-4(1H)-pyridinone 34737-89-8 C13H17NO 详情 详情
(II) 14720 3-methyltetrahydro-4(1H)-pyridinone C6H11NO 详情 详情
(III) 14721 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one C5H9BrN4O 详情 详情
(IV) 14722 1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetraazol-1-yl)ethyl]-3-methyltetrahydro-4(1H)-pyridinone C11H19N5O2 详情 详情
(V) 14723 4-Bromo-2-fluorophenylamine; 4-Bromo-2-fluoroaniline 367-24-8 C6H5BrFN 详情 详情
(VI) 14724 1-[2-[4-(4-bromo-2-fluoroanilino)-3-methylpiperidino]ethyl]-4-ethyl-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one C17H24BrFN6O 详情 详情
(VII) 13429 2-Methoxyacetyl chloride; Methoxyacetyl chloride 38870-89-2 C3H5ClO2 详情 详情
(VIII) 14726 N-(4-bromo-2-fluorophenyl)-N-[(3R,4S)-1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetraazol-1-yl)ethyl]-3-methylhexahydro-4-pyridinyl]-2-methoxyacetamide C20H28BrFN6O3 详情 详情
Extended Information