2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid -Drug Synthesis Database

【结构式】

【分子编号】64718

【品名】2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid

【CA登记号】

【分子式】C₁₂H₁₇N₃O₅S

【分子量】315.3502

【元素组成】C 45.71% H 5.43% N 13.32% O 25.37% S 10.17%

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：(XIV)

The acid chloride (X) is condensed with cyclopropylmethylamine (XI) to produce the sulfonamide (XII). Subsequent acidic Boc group cleavage in (XII) leads to the amine (XIII). Alkaline hydrolysis of the ethyl ester group of (XIII) provides the acid (XIV), which is subsequently coupled to 6-amino-3-(aminomethyl)-2-methylpyridine (XV) by means of EDC/HOAt to yield the amide (XVI). Finally, condensation of (XVI) with HCHO, followed by cyclization either in the presence of EDC or under acidic conditions, furnishes the target pyridothiadiazine. (1,2)

参考文献中间体

合成目标

【1】 Sanderson, P.E.J.; Cutrona, K.J.; Savage, K.L.; Naylor-Olsen, A.M.; Bickel, D.J.; Bohn, D.L.; Clayton, F.C.; Krueger, J.A.; Lewis, S.D.; Lucas, B.J.; Lyle, E.A.; Wallace, A.A.; Welsh, D.C.; Yan, Y.; 3-Amino-4-sulfonylpyridinone acetamide and related pyridothiadiazine thrombin inhibitors. Bioorg Med Chem Lett 2003, 13, 8, 1441.
【2】 Sanderson, P.E.; Cutrona, K. (Merck & Co., Inc.); Thrombin inhibitors. EP 1117660; JP 2002525370; US 6117888; WO 0018762 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	64715	ethyl 2-[3-[bis(tert-butoxycarbonyl)amino]-4-(chlorosulfonyl)-6-methyl-2-oxo-1(2H)-pyridinyl]acetate		C₂₀H₂₉ClN₂O₉S	详情	详情
(XI)	59524	Aminomethylcyclopropane; Cyclopropanemethylamine	2516-47-4	C₄H₉N	详情	详情
(XII)	64716	ethyl 2-[3-[bis(tert-butoxycarbonyl)amino]-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetate		C₂₄H₃₇N₃O₉S	详情	详情
(XIII)	64717	ethyl 2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetate		C₁₄H₂₁N₃O₅S	详情	详情
(XIV)	64718	2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid		C₁₂H₁₇N₃O₅S	详情	详情
(XV)	18339	5-(aminomethyl)-6-methyl-2-pyridinamine; 5-(aminomethyl)-6-methyl-2-pyridinylamine		C₇H₁₁N₃	详情	详情
(XVI)	64719	2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]-N-[(6-amino-2-methyl-3-pyridinyl)methyl]acetamide		C₁₉H₂₆N₆O₄S	详情	详情

Extended Information