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【结 构 式】

【分子编号】26413

【品名】N-(5-formyl-2-pyridinyl)acetamide

【CA登记号】

【 分 子 式 】C8H8N2O2

【 分 子 量 】164.1638

【元素组成】C 58.53% H 4.91% N 17.06% O 19.49%

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:(X)

The condensation of 2-methylquinolin-8-ol (I) with 2,6-dichloro-3-nitrobenzyl chloride (II) by means of NaH in DMF gives the corresponding benzyl ether (III), which is reduced with Fe and HCl in methanol/water to the aniline (IV). The acylation of (IV) with 2-phthalimidoacetyl chloride (V) by means of DMAP and pyridine yields the amide (VI), which is methylated at the amidic nitrogen with NaH and methyl iodide in DMF to the N-methylanilide (VII). Elimination of the phthalimido group of (VII) with hydrazine in refluxing ethanol affords the glycine anilide (VIII), which is acylated with the acrylic acid (IX) by means of 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide (DECD) and HOBT in DMF. The intermediate substituted acrylic acid (IX) has been obtained by reaction of 6-acetamidopyridine-3-carbaldehyde (X) with malonic acid and pyridine in refluxing ethanol.

1 Oku, T.; Kayakiri, H.; Satoh, S.; Abe, Y.; Sawada, Y.; Inoue, T.; Tanaka, H. (Fujisawa Pharmaceutical Co., Ltd.); Pyridopyrimidones, quinolines and fused N-heterocycles as bradykinin antagonists. EP 0807105; JP 1998507764; WO 9613485 .
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) 18598 2-methyl-8-quinolinol 826-81-3 C10H9NO 详情 详情
(II) 18928 1,3-dichloro-2-(chloromethyl)-4-nitrobenzene C7H4Cl3NO2 详情 详情
(III) 18929 2,6-dichloro-3-nitrobenzyl 2-methyl-8-quinolinyl ether; 8-[(2,6-dichloro-3-nitrobenzyl)oxy]-2-methylquinoline C17H12Cl2N2O3 详情 详情
(IV) 18930 2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenylamine; 2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]aniline C17H14Cl2N2O 详情 详情
(V) 10278 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride 6780-38-7 C10H6ClNO3 详情 详情
(VI) 18932 N-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetamide C27H19Cl2N3O4 详情 详情
(VII) 18599 N-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-methylacetamide C28H21Cl2N3O4 详情 详情
(VIII) 18600 2-amino-N-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-N-methylacetamide C20H19Cl2N3O2 详情 详情
(IX) 19304 (E)-3-[6-(acetamido)-3-pyridinyl]-2-propenoic acid C10H10N2O3 详情 详情
(X) 26413 N-(5-formyl-2-pyridinyl)acetamide C8H8N2O2 详情 详情
(XI) 12963 Malonic acid 141-82-2 C3H4O4 详情 详情
Extended Information