6-amino-2,2-dimethyl-2H-1,4-benzothiazin-3(4H)-one -Drug Synthesis Database

【结构式】

【分子编号】45974

【品名】6-amino-2,2-dimethyl-2H-1,4-benzothiazin-3(4H)-one

【CA登记号】

【分子式】C₁₀H₁₂N₂OS

【分子量】208.28416

【元素组成】C 57.67% H 5.81% N 13.45% O 7.68% S 15.4%

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：(IV)

Alkylation of 2,4-dinitrothiophenol (I) with 2-bromoisobutyrate (II) and K2CO3 in DMF yields thioether (III), which is then subjected to reduction with Fe/HCl in EtOH/H2O, followed by ring closure with refluxing NaOH, to give benzothiazine derivative (IV). Conversion of amino compound (IV) into nitro derivative (V) is then performed via Sandmeyer reaction by first treatment with NaNO2/H2SO4 in H2O, followed by reaction with NaHCO3, NaNO2, CuSO4 and Cu2O in H2O. N-Alkylation of (V) with chloroacetone (VI) and K2CO3 in DMF provides (VII), which is finally converted into the target compound by reduction with BH3-THF complex in THF, followed by Swern oxidation with DMSO and oxalyl chloride in CH2Cl2.

参考文献中间体

合成目标

【1】 Yoden, T.; Matsuhisa, A.; Yamagiwa, Y.; Nohira, H.; Tsuzuki, R.; Yanagisawa, I.; Matsumoto, Y.; Shibanuma, T.; Novel potassium channel openers. Part 4: Transformation of the 1,4-benzoxazine skeleton into 1,4-benzothiazine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroquinoxaline, indoline, and 1,5-benzoxazepine. Bioorg Med Chem 2000, 8, 2, 393.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	45972	2,4-dinitrobenzenethiol; 2,4-dinitrophenylhydrosulfide		C₆H₄N₂O₄S	详情	详情
(II)	39799	ethyl 2-bromo-2-methylpropanoate	600-00-0	C₆H₁₁BrO₂	详情	详情
(III)	45973	ethyl 2-[(2,4-dinitrophenyl)sulfanyl]-2-methylpropanoate		C₁₂H₁₄N₂O₆S	详情	详情
(IV)	45974	6-amino-2,2-dimethyl-2H-1,4-benzothiazin-3(4H)-one		C₁₀H₁₂N₂OS	详情	详情
(V)	45975	2,2-dimethyl-6-nitro-2H-1,4-benzothiazin-3(4H)-one		C₁₀H₁₀N₂O₃S	详情	详情
(VI)	15288	1-Chloroacetone; Chloroacetone	78-95-5	C₃H₅ClO	详情	详情
(VII)	45976	2,2-dimethyl-6-nitro-4-(2-oxopropyl)-2H-1,4-benzothiazin-3(4H)-one		C₁₃H₁₄N₂O₄S	详情	详情

Extended Information