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【结 构 式】 
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【分子编号】50956 【品名】2-[4-(2-chloroethyl)-7-fluoro-2-oxo-1(2H)-quinolinyl]acetamide 【CA登记号】 |
【 分 子 式 】C13H12ClFN2O2 【 分 子 量 】282.7016632 【元素组成】C 55.23% H 4.28% Cl 12.54% F 6.72% N 9.91% O 11.32% |
合成路线1
该中间体在本合成路线中的序号：(IX)The alkylation of 3-fluoroaniline (I) with 2-bromoacetamide (II) by means of KOH and Bu4NBr in THF gives 2-(3-fluorophenylamino)acetamide (III), which is condensed with 4-acetoxy-3,6-dihydro-2H-pyran-2,6-dione (IV) in Ac-OH to yield intermediate (V). The cyclization of (V) by means of H2SO4 or Ms-OH at 100?C affords the quinolone (VII), which is esterified with SOCl2 and methanol to provide the corresponding methyl ester (VII). The reduction of (VII) with NaBH4 in refluxing THF furnishes the 2-hydroxyethyl quinolone (VIII), which is treated with SOCl2 in refluxing CHCl3 to give the 2-chloroethyl derivative (IX). Finally, this compound is condensed with the arylpiperazine (X) by means of K2CO3 and KI in hot DMF to afford the desired quinolone.
| 【1】 McCort, G.; et al.; Synthesis and SAR of 3- and 4-substituted quinolin-2-ones: Discovery of mixed 5-HT1b/5-HT2A receptor antagonists. Bioorg Med Chem 2001, 9, 8, 2129. |
| 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) | 20697 | 3-fluoroaniline; 3-fluorophenylamine | 372-19-0 | C6H6FN | 详情 | 详情 |
| (II) | 38747 | 2-bromoacetamide | 683-57-8 | C2H4BrNO | 详情 | 详情 |
| (III) | 50951 | 2-(3-fluoroanilino)acetamide | C8H9FN2O | 详情 | 详情 | |
| (IV) | 40692 | 2,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetate | C7H6O5 | 详情 | 详情 | |
| (V) | 50952 | (Z)-3-(acetoxy)-5-[(2-amino-2-oxoethyl)-3-fluoroanilino]-5-oxo-2-pentenoic acid | C15H15FN2O6 | 详情 | 详情 | |
| (VI) | 50953 | 2-[1-(2-amino-2-oxoethyl)-7-fluoro-2-oxo-1,2-dihydro-4-quinolinyl]acetic acid | C13H11FN2O4 | 详情 | 详情 | |
| (VII) | 50954 | methyl 2-[1-(2-amino-2-oxoethyl)-7-fluoro-2-oxo-1,2-dihydro-4-quinolinyl]acetate | C14H13FN2O4 | 详情 | 详情 | |
| (VIII) | 50955 | 2-[7-fluoro-4-(2-hydroxyethyl)-2-oxo-1(2H)-quinolinyl]acetamide | C13H13FN2O3 | 详情 | 详情 | |
| (IX) | 50956 | 2-[4-(2-chloroethyl)-7-fluoro-2-oxo-1(2H)-quinolinyl]acetamide | C13H12ClFN2O2 | 详情 | 详情 | |
| (X) | 40698 | 4-(1-piperazinyl)thieno[3,2-c]pyridine | C11H13N3S | 详情 | 详情 |