methyl 2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1lambda(6),2-benzothiazine-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】40064

【品名】methyl 2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1lambda(6),2-benzothiazine-3-carboxylate

【CA登记号】

【分子式】C₁₁H₁₁NO₅S

【分子量】269.27808

【元素组成】C 49.06% H 4.12% N 5.2% O 29.71% S 11.91%

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：(III)

The isomerization of methyl 3-oxo-1,2-benzothiazolin-1,1-dioxide-2-acetate (I) by means of sodium methoxide in DMSO gives methyl 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-1,1-dioxide-3-carboxylate (II), which is methylated with methyl iodide and NaOH in methanol giving methyl 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-1,1-dioxide-3-carboxylate (III). Finally, this product is treated with 2-aminopyridine (A) in refluxing xylene.

参考文献中间体

合成目标

【1】 Arrigoni-Martelli, E.; Castaner, J.; Piroxicam. Drugs Fut 1977, 2, 2, 124.
【2】 Lombardino, J.G.; et al.; Potent anti-inflammatory N-heterocyclic 3-carboxamides of 4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide. J Med Chem 1973, 16, 5, 493.
【3】 Lombardino, J.G.; Wiseman, E.H.; Sudoxicam and related N.heterocyclic carboxamides of 4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide, potent non steroidal anti-inflammatory agents. J Med Chem 1972, 15, 8, 848.
【4】 Lombardino, J.G. (Pfizer Inc.); Benzothiazine dioxides. DE 1943265; FR 2016455; GB 1257180; US 3591584 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	11305	2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine	504-29-0	C₅H₆N₂	详情	详情
(I)	40062	methyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate	6639-62-9	C₁₀H₉NO₅S	详情	详情
(II)	40063	methyl 1,1,4-trioxo-1,2,3,4-tetrahydro-1lambda(6),2-benzothiazine-3-carboxylate		C₁₀H₉NO₅S	详情	详情
(III)	40064	methyl 2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1lambda(6),2-benzothiazine-3-carboxylate		C₁₁H₁₁NO₅S	详情	详情

Extended Information