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【结 构 式】

【分子编号】26602

【品名】2-hydroxy-6-methylnicotinic acid

【CA登记号】38116-61-9

【 分 子 式 】C7H7NO3

【 分 子 量 】153.13752

【元素组成】C 54.9% H 4.61% N 9.15% O 31.34%

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:(IX)

The intermediate 2-[3-(benzylsulfonamido)-6-methyl-2-oxo-1,2-dihydropyridin-1-yl]acetic acid (VI) has been obtained as follows: The reaction of 2-hydroxy-6-methylpyridine-3-carboxylic acid (IX) with diphenylphosphoryl azide (DPPA), triethylamine and benzyl alcohol in refluxing dioxane gives 3-(benzyloxycarbonylamino)-6-methylpyridin-2(1H)-one (X), which is condensed with tert-butyl bromoacetate (II) by means of NaH in THF yielding the expected condensation product (XI). The deprotection od the amino group of (XI) with H2 over Pd/C in ethanol/water gives the aminopyridone (XII), which is acylated with benzylsulfonylchloride (XIII) in pyridine yielding the sulfonamide (XIV). Finally, the tert-butyl ester group of (XIV) is hydrolyzed with HCl in ethyl acetate to afford the target intermediate (VI).

1 Naylor-Olsen, A.M.; Newton, C.L.; Isaacs, R.C.A.; Dorsey, B.D. (Merck & Co., Inc.); Thrombin inhibitors. EP 0969840; US 5932606; WO 9842342 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 26599 2-[3-[(benzylsulfonyl)amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid C15H16N2O5S 详情 详情
(IX) 26602 2-hydroxy-6-methylnicotinic acid 38116-61-9 C7H7NO3 详情 详情
(X) 26603 benzyl 6-methyl-2-oxo-1,2-dihydro-3-pyridinylcarbamate C14H14N2O3 详情 详情
(XI) 26604 tert-butyl 2-[3-[[(benzyloxy)carbonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetate C20H24N2O5 详情 详情
(XII) 26605 tert-butyl 2-[3-amino-6-methyl-2-oxo-1(2H)-pyridinyl]acetate C12H18N2O3 详情 详情
(XIII) 25151 phenylmethanesulfonyl chloride 1939-99-7 C7H7ClO2S 详情 详情
(XIV) 26606 tert-butyl 2-[3-[(benzylsulfonyl)amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetate C19H24N2O5S 详情 详情
Extended Information