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【结 构 式】

【分子编号】57032

【品名】3-fluoro-2-naphthalenamine; 3-fluoro-2-naphthylamine

【CA登记号】

【 分 子 式 】C10H8FN

【 分 子 量 】161.1786632

【元素组成】C 74.52% H 5% F 11.79% N 8.69%

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:(VI)

3-Amino-2-naphthoic acid (I) is diazotized with NaNO2/HCl, and the obtained diazonium salt is then isolated as the corresponding tetrafluoroborate (II). Subsequent thermal decomposition of the diazonium tetrafluoroborate (II) in refluxing xylene leads to 3-fluoro-2-naphthoic acid (III). After chlorination of (III) with oxalyl chloride, the resultant acid chloride (IV) is treated with NaN3 to produce the acyl azide (V), which undergoes Curtius rearrangement to the amine (VI) in refluxing aqueous DMF. Diazotization of (VI), followed by reduction with SnCl2 gives rise to hydrazine (VII). Treatment of ethyl 2,4-dioxovalerate (VIII) with O-methylhydroxylamine gives oxime (IX), which is then condensed with hydrazine (VII), yielding the intermediate pyrazole (X).

1 Jia, Z.J.; et al.; Design, synthesis and biological activity of novel non-amidine factor Xa inhibitors: Part 1: Structure-activity relationships of the substituted 1-(2-naphthyl)-1H-pyrazole-5-carboxylamides. Bioorg Med Chem Lett 2002, 12, 12, 1651.
2 Wang, L.; Zhu, B.-Y.; Li, W.; Zhang, P.; Huang, W.; Song, Y.; Goldman, E.; Zuckett, J.; Scarborough, R. (Millennium Pharmaceuticals, Inc.); Benzamides and related inhibitors of factor Xa. EP 1216228; EP 1216231; WO 0119788; WO 0119798 .
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) 47431 3-amino-2-naphthoic acid 5959-52-4 C11H9NO2 详情 详情
(II) 57028   C11H7BF4N2O2 详情 详情
(III) 57029 3-fluoro-2-naphthoic acid C11H7FO2 详情 详情
(IV) 57030 3-fluoro-2-naphthoyl chloride C11H6ClFO 详情 详情
(V) 57031 3-fluoro-2-naphthoyl azide C11H6FN3O 详情 详情
(VI) 57032 3-fluoro-2-naphthalenamine; 3-fluoro-2-naphthylamine C10H8FN 详情 详情
(VII) 57033 1-(3-fluoro-2-naphthyl)hydrazine C10H9FN2 详情 详情
(VIII) 42500 ethyl 2,4-dioxopentanoate 615-79-2 C7H10O4 详情 详情
(IX) 44129 ethyl 2-(methoxyimino)-4-oxopentanoate C8H13NO4 详情 详情
(X) 57034 ethyl 1-(3-fluoro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate C17H15FN2O2 详情 详情
Extended Information