7-hydroxy-2H-1,4-benzothiazin-3(4H)-one -Drug Synthesis Database

【结构式】

【分子编号】28290

【品名】7-hydroxy-2H-1,4-benzothiazin-3(4H)-one

【CA登记号】

【分子式】C₈H₇NO₂S

【分子量】181.21512

【元素组成】C 53.02% H 3.89% N 7.73% O 17.66% S 17.69%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(V)

Alkylation of 3-hydroxybenzyl alcohol (II) with 2-chloromethylquinazoline (I) in the presence of K2CO3 and tetrabutylammonium bromide provided ether (III). The hydroxyl group of (III) was converted to chloride (IV) by treatment with thionyl chloride. Finally, alkylation of hydroxybenzothiazinone (V) with chloride (IV) yielded the title compound.

参考文献中间体

合成目标

【1】 Tamura, M.; Tohma, T.; Onogi, K.; et al.; VUF-K-8707 and analogs, non-acidic leukotriene D4 receptor antagonists. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.226.
【2】 Timmerman, H.; Zhang, M.; Onogi, K.; Tamura, M.; Toma, T.; Wada, Y. (Kowa Co., Ltd.); Heteroaryl substd. phenylene derivs., their preparation and their use a leukotriene receptor antagonists. EP 0799826; JP 1997323975; US 5756518; US 5885987; US 6011033 .

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)	28285	2-(chloromethyl)quinazoline		C₉H₇ClN₂	详情	详情
(II)	17296	3-Hydroxybenzyl alcohol; 3-(hydroxymethyl)phenol	620-24-6	C₇H₈O₂	详情	详情
(III)	28286	[3-(2-quinazolinylmethoxy)phenyl]methanol		C₁₆H₁₄N₂O₂	详情	详情
(IV)	28287	2-[[3-(chloromethyl)phenoxy]methyl]quinazoline		C₁₆H₁₃ClN₂O	详情	详情
(V)	28290	7-hydroxy-2H-1,4-benzothiazin-3(4H)-one		C₈H₇NO₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Alkylation of 3-hydroxybenzyl alcohol (II) with benzimidazolylmethyl chloride (I) in the presence of K2CO3 and tetrabutylammonium bromide provided ether (III). The hydroxyl group of (III) was converted to chloride (IV) by treatment with thionyl chloride. Finally, alkylation of hydroxybenzothiazinone (V) with chloride (IV) yielded the title compound.

参考文献中间体

合成目标

【1】 Tamura, M.; Tohma, T.; Onogi, K.; et al.; VUF-K-8707 and analogs, non-acidic leukotriene D4 receptor antagonists. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.226.
【2】 Timmerman, H.; Zhang, M.; Onogi, K.; Tamura, M.; Toma, T.; Wada, Y. (Kowa Co., Ltd.); Heteroaryl substd. phenylene derivs., their preparation and their use a leukotriene receptor antagonists. EP 0799826; JP 1997323975; US 5756518; US 5885987; US 6011033 .

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)	28288	2-(chloromethyl)-1-(2-ethoxyethyl)-1H-benzimidazole		C₁₂H₁₅ClN₂O	详情	详情
(II)	17296	3-Hydroxybenzyl alcohol; 3-(hydroxymethyl)phenol	620-24-6	C₇H₈O₂	详情	详情
(III)	28289	(3-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]methoxy]phenyl)methanol		C₁₉H₂₂N₂O₃	详情	详情
(IV)	28291	2-[[3-(chloromethyl)phenoxy]methyl]-1-(2-ethoxyethyl)-1H-benzimidazole		C₁₉H₂₁ClN₂O₂	详情	详情
(V)	28290	7-hydroxy-2H-1,4-benzothiazin-3(4H)-one		C₈H₇NO₂S	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VII)

The alkylation of N-formylpiperazine (II) with 2-(chloromethyl)quinoline (I) produced the disubstituted piperazine (III). The formyl group of (III) was then cleaved by means of H2SO4 in boiling EtOH, yielding quinolylmethylpiperazine (IV). Subsequent alkylation of (IV) with 1-bromo-3-chloropropane (V) afforded the chloropropyl derivative (VI). This was finally condensed with 7-hydroxybenzothiazinone (VII) in the presence of K2CO3 and a phase-transfer catalyst to furnish the title compound.

参考文献中间体

合成目标

【1】 Tohma, T.; Onogi, K.; Zang, M.; Timmerman, H.; Wada, Y.; Tamura, M. (Kowa Co., Ltd.); Diamine derivs. and pharmaceutical containing the same. EP 0957100; WO 9902520 .

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)	13162	2-(Chloromethyl)quinoline; alpha-Chloroquinaldine	4377-41-7	C₁₀H₈ClN	详情	详情
(II)	23801	1-piperazinecarbaldehyde; N-Formylpiperazine	7755-92-2	C₅H₁₀N₂O	详情	详情
(III)	41113	4-(2-quinolinylmethyl)-1-piperazinecarbaldehyde		C₁₅H₁₇N₃O	详情	详情
(IV)	41114	2-(1-piperazinylmethyl)quinoline		C₁₄H₁₇N₃	详情	详情
(V)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(VI)	41115	2-[[4-(3-chloropropyl)-1-piperazinyl]methyl]quinoline		C₁₇H₂₂ClN₃	详情	详情
(VII)	28290	7-hydroxy-2H-1,4-benzothiazin-3(4H)-one		C₈H₇NO₂S	详情	详情

Extended Information