4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-2H-thieno[2,3-b]thiopyran-6-sulfonamide -Drug Synthesis Database

【结构式】

【分子编号】21040

【品名】4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-2H-thieno[2,3-b]thiopyran-6-sulfonamide

【CA登记号】

【分子式】C₇H₉NO₅S₃

【分子量】283.3502

【元素组成】C 29.67% H 3.2% N 4.94% O 28.23% S 33.95%

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：(I)

The reaction of (I) with acetonitrile in sulfuric acid provides the amide (II), which after hydrolysis in 12N HCl/methanol yields the 4-amino derivative (III). Acylation of (III) with isobutyryl chloride followed by reduction with borane-methylsulfide complex gives the racemate (V), MK-927 (2). The resolution of MK-927 is accomplished through the di-p-toluoyl-D-tartaric acid salt.

参考文献中间体

合成目标

【1】 Baldwin, J.J.; Christy, M.E.; Ponticello, G.S.; Anyiglaucoma thieno-thiopyran and thieno-thiepin sulfonamide derivatives, compositions, and method of use thereof.. US 4677115 .
【2】 Baldwin, J.J.; Ponticello, G.S.; Sugrue, M.F.; MK-417. Drugs Fut 1989, 14, 7, 636.
【3】 Ponticello, G.S.; Freedman, M.B.; Habecker, C.N.; Lyle, P.A.; Schwam, H.; Varga, S.L.; Christy, M.E.; Randall, W.C.; Baldwin, J.J.; Thienothiopyran-2-sulfonamides: A novel class of water-soluble carbonic anhydrase inhibitors. J Med Chem 1987, 30, 591-7.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	14932	isobutyryl chloride; 2-methylpropanoyl chloride	79-30-1	C₄H₇ClO	详情	详情
(I)	21040	4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-2H-thieno[2,3-b]thiopyran-6-sulfonamide		C₇H₉NO₅S₃	详情	详情
(II)	21041	N-[6-(aminosulfonyl)-1,1-dioxo-1,2,3,4-tetrahydro-2H-thieno[2,3-b]thiopyran-4-yl]acetamide		C₉H₁₂N₂O₅S₃	详情	详情
(III)	21042	4-amino-1,1-dioxo-1,2,3,4-tetrahydro-2H-thieno[2,3-b]thiopyran-6-sulfonamide		C₇H₁₀N₂O₄S₃	详情	详情
(IV)	21043	N-[6-(aminosulfonyl)-1,1-dioxo-1,2,3,4-tetrahydro-2H-thieno[2,3-b]thiopyran-4-yl]-2-methylpropanamide		C₁₁H₁₆N₂O₅S₃	详情	详情
(V)	21044	4-(isobutylamino)-1,1-dioxo-1,2,3,4-tetrahydro-2H-thieno[2,3-b]thiopyran-6-sulfonamide		C₁₁H₁₈N₂O₄S₃	详情	详情

Extended Information