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【结 构 式】

【分子编号】28301

【品名】1,5-dichloro-2-nitro-4-(trifluoromethyl)benzene

【CA登记号】400-70-4

【 分 子 式 】C7H2Cl2F3NO2

【 分 子 量 】259.9990296

【元素组成】C 32.34% H 0.78% Cl 27.27% F 21.92% N 5.39% O 12.31%

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:(I)

The reaction of 2,4-dichloro-5-(trifluoromethyl)nitrobenzene (I) with aminomethanephosphonic acid (II) by means of NaOH in ethanol/water gives the anilinomethanephosphonic acid (III), which is condensed first with morpholine (IV) by heating at 120 C and esterified with triethyl orthoformate at 150 C yielding 5-(4-morpholinyl)-2-nitro-4-(trifluoromethyl)phenylaminomethyl phosphonic acid diethyl ester (V). The reduction of the nitro group of (V) with H2 over Pd/C in ethanol affords the corresponding amino-derivative (VI), which is cyclized with oxalic acid monoethyl ester monochloride (VII) by means of triethylamine in THF providing the quinoxaline (VIII). Finally, this compound is hydrolyzed to the free phosphonic acid with trimethylbromo silane in acetonitrile.

1 Huth, A.; Turski, L. (Schering AG); Quinoxalindione derivs., their preparation and their use in drugs. DE 4314591; DE 4344486; EP 0696288; EP 1002796; JP 1996508037; US 5750525; WO 9425469 .
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) 28301 1,5-dichloro-2-nitro-4-(trifluoromethyl)benzene 400-70-4 C7H2Cl2F3NO2 详情 详情
(II) 28302 aminomethylphosphonic acid 1066-51-9 CH6NO3P 详情 详情
(III) 28303 [5-chloro-2-nitro-4-(trifluoromethyl)anilino]methylphosphonic acid C8H7ClF3N2O5P 详情 详情
(IV) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(V) 28304 diethyl [5-(4-morpholinyl)-2-nitro-4-(trifluoromethyl)anilino]methylphosphonate C16H23F3N3O6P 详情 详情
(VI) 28305 diethyl [2-amino-5-(4-morpholinyl)-4-(trifluoromethyl)anilino]methylphosphonate C16H25F3N3O4P 详情 详情
(VII) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(VIII) 28306 diethyl [7-(4-morpholinyl)-2,3-dioxo-6-(trifluoromethyl)-3,4-dihydro-1(2H)-quinoxalinyl]methylphosphonate C18H23F3N3O6P 详情 详情
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