7-propionyl-2H-1,4-benzoxazin-3(4H)-one -Drug Synthesis Database

【结构式】

【分子编号】41301

【品名】7-propionyl-2H-1,4-benzoxazin-3(4H)-one

【CA登记号】

【分子式】C₁₁H₁₁NO₃

【分子量】205.21328

【元素组成】C 64.38% H 5.4% N 6.83% O 23.39%

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)

The acylation of benzoxazolin-2-one (I) with propionic anhydride (II) by means of P2O5 and MsOH gives 6-propionylbenzoxazolin-2-one (III), which is treated with chloroacetyl chloride to yield 7-propionyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (IV). The Mannich condensation of (IV) with CH2O and NH3 followed by methylation with methyl iodide affords the trimethylammonium compound (V), which by reaction with KCN, followed by hydrolysis with HCl gives 3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarbonyl)butyric acid (VI). Finally this compound is cyclized with hydrazine to furnish the target pyridazinone.

参考文献中间体

合成目标

【1】 Bonte, J.P.; Lesier, D.; Lespagnol, C.; et al.; 6-Acyl benzoxazolinones. I. Eur J Med Chem - Chim Ther 1974, 9, 491.
【2】 Kryvenko, M.; Techer, H.; Lavergne, M.; et al.; Electrophilic substitutions of 2H-1,4-benzoxazine-3-one: Acylation and chlorosulfonation. CR Acad Sci Paris Ser C 1970, 270, 19, 1601.
【3】 Lesier, D.; Lespagnol, C.; Bonte, J.P.; et al.; 6-Acyl benzoxazolinones. II. Preparation of some transformation products. Eur J Med Chem - Chim Ther 1974, 9, 497-500.
【4】 Thyes, M.; Lehmann, H.D.; Gries, J.; et al.; 6-Aryl-4,5-dihydro-3(2H)-pyridazinones. A new class of compounds with platelet aggregation inhibiting and hypotensive activities. J Med Chem 1983, 26, 6, 800.
【5】 Moussavi, Z.; Lesieur, D.; Depreux, P.; An aternative synthesis of cardiotonic 6-(3,4-dihydro-3-oxo-1,4[2H]benzoxazin-7-yl)-2,3,4,5-tetrahydro-5-methylpyridazin-3-ones. Synth Commun 1991, 21, 2, 271.
【6】 Combs, D.W.; Bemoradan and related pyridazinone cardiotonics. Drugs Fut 1993, 18, 2, 139.

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)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(I)	41299	2-Benzoxazolinone; 2(3H)-benzoxazolone; 1,3-benzoxazol-2(3H)-one	59-49-4	C₇H₅NO₂	详情	详情
(II)	20095	propionic anhydride	123-62-6	C₆H₁₀O₃	详情	详情
(III)	41300	6-propionyl-1,3-benzoxazol-2(3H)-one		C₁₀H₉NO₃	详情	详情
(IV)	41301	7-propionyl-2H-1,4-benzoxazin-3(4H)-one		C₁₁H₁₁NO₃	详情	详情
(V)	41302	N,N,N,2-tetramethyl-3-oxo-3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-propanaminium		C₁₅H₂₁N₂O₃	详情	详情
(VI)	41303	3-methyl-4-oxo-4-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)butyric acid		C₁₃H₁₃NO₅	详情	详情

Extended Information