7-chloro-2-propyl-4H-3,1-benzoxazin-4-one -Drug Synthesis Database

【结构式】

【分子编号】58446

【品名】7-chloro-2-propyl-4H-3,1-benzoxazin-4-one

【CA登记号】

【分子式】C₁₁H₁₀ClNO₂

【分子量】223.65864

【元素组成】C 59.07% H 4.51% Cl 15.85% N 6.26% O 14.31%

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)

4-Chloroanthranilic acid (I) is acylated by butyryl chloride (II) in DMF to produce amide (III). This is then cyclized to the benzoxazinone (IV) upon heating with acetic anhydride. Condensation of (IV) with benzylamine (V) in refluxing chloroform, followed by treatment with NaOH in hot ethyleneglycol, gives rise to the quinazolinone (VI). Subsequent benzylic bromination of (VI) at the propyl side chain produces (VII). The bromide group of (VII) is then displaced with N,N-dimethyl-1,3-propanediamine (VIII) to furnish (IX). Finally, amine (IX) is acylated by 4-bromobenzoyl chloride (X) to afford the corresponding benzamide.

参考文献中间体

合成目标

【1】 Chabala, J.C.; Morgans, D.J. Jr.; Feng, B.; Finer, J.T.; Bergnes, G.; Smith, W.W. (Cytokinetics, Inc.); Methods and compsns. utilizing quinazolinones. WO 0198278 .

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)	52504	4-Chloro-2-aminobenzoic acid; 2-Amino-4-chlorobenzoic acid; 2-Carboxy-5-chloroaniline; 3-Amino-4-carboxy-1-chlorobenzene; 4-Chloroanthranilic acid	89-77-0	C₇H₆ClNO₂	详情	详情
(II)	10792	Butanoyl chloride; Butyryl chloride	141-75-3	C₄H₇ClO	详情	详情
(III)	58445	2-(butyrylamino)-4-chlorobenzoic acid		C₁₁H₁₂ClNO₃	详情	详情
(IV)	58446	7-chloro-2-propyl-4H-3,1-benzoxazin-4-one		C₁₁H₁₀ClNO₂	详情	详情
(V)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(VI)	58447	3-benzyl-7-chloro-2-propyl-4(3H)-quinazolinone		C₁₈H₁₇ClN₂O	详情	详情
(VII)	58448	3-benzyl-2-(1-bromopropyl)-7-chloro-4(3H)-quinazolinone		C₁₈H₁₆BrClN₂O	详情	详情
(VIII)	25248	N-(3-aminopropyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,3-propanediamine	109-55-7	C₅H₁₄N₂	详情	详情
(IX)	58449	3-benzyl-7-chloro-2-(1-{[3-(dimethylamino)propyl]amino}propyl)-4(3H)-quinazolinone		C₂₃H₂₉ClN₄O	详情	详情
(X)	45960	4-bromobenzoyl chloride	586-75-4	C₇H₄BrClO	详情	详情

Extended Information