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【结 构 式】

【分子编号】26603

【品名】benzyl 6-methyl-2-oxo-1,2-dihydro-3-pyridinylcarbamate

【CA登记号】

【 分 子 式 】C14H14N2O3

【 分 子 量 】258.27684

【元素组成】C 65.11% H 5.46% N 10.85% O 18.58%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(X)

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

合成路线2

该中间体在本合成路线中的序号:(XI)

Synthesis of intermediate (VI): Treatment of pyridone (X) with diphenyl phosphoryl azide (DPPA) followed by reaction with benzyl alcohol affords the protected derivative (XI), which then reacts with tert-butyl bromoacetate (XII) by means of Cs2CO3 to provide the acetate derivative (XIII). Hydrogenation of (XIII) over Pd/C allows Cbz removal, giving amine (XIV), which is then condensed with iodo derivative (XV) to furnish sulfonamide compound (XVI). Finally, hydrolysis of (XVI) is achieved by treatment with TFA to afford the target intermediate (VI).

1 Soll, R.M.; Lu, T.; Tomczuk, B.E.; Spurlino, J.; Pan, W.; Bone, R.; Green, D.W.; Heteroaryl keto thrombin inhibitors: Design and synthesis. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 285.
2 Tumczuk, B.E.; Pan, W.; Soll, R.M.; Lu, T. (3-Dimensional Pharmaceuticals, Inc.); Heteroaryl protease inhibitors and diagnostic imaging agents. WO 0104117 .
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) 44786 2-[3-[[(2-iodobenzyl)sulfonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid C15H15IN2O5S 详情 详情
(X) 44789 6-methyl-2-oxo-1,2-dihydro-3-pyridinecarboxylic acid C7H7NO3 详情 详情
(XI) 26603 benzyl 6-methyl-2-oxo-1,2-dihydro-3-pyridinylcarbamate C14H14N2O3 详情 详情
(XII) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(XIII) 26604 tert-butyl 2-[3-[[(benzyloxy)carbonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetate C20H24N2O5 详情 详情
(XIV) 26605 tert-butyl 2-[3-amino-6-methyl-2-oxo-1(2H)-pyridinyl]acetate C12H18N2O3 详情 详情
(XV) 44791 (2-iodophenyl)methanesulfonyl chloride C7H6ClIO2S 详情 详情
(XVI) 44790 tert-butyl 2-[3-[[(2-iodobenzyl)sulfonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetate C19H23IN2O5S 详情 详情
Extended Information