6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione -Drug Synthesis Database

【结构式】

【分子编号】18007

【品名】6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione

【CA登记号】25983-13-5

【分子式】C₈H₄Cl₂N₂O₂

【分子量】231.03744

【元素组成】C 41.59% H 1.75% Cl 30.69% N 12.13% O 13.85%

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：(VIII)

Alternatively, condensation of phenylenediamine (IV) with oxalate (III) in hot sulfuric acid afforded labeled quinoxalinedione (VIII), to which was added acetic acid or diethyl oxalate in order to protect amino groups, and was then nitrated with fuming nitric acid and sulfuric acid.

参考文献中间体

合成目标

【1】 Thorell, J.O.; et al.; Synthesis of a C-11-labelled nitrated 1,4-dihydroquinoxaline-2,3-dione, the NMDA glycine receptor antagonist ACEA 1021 (Licostinel). J Label Compd Radiopharm 1998, 41, 4, 345-353.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	17571	Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate	95-92-1	C₆H₁₀O₄	详情	详情
(III)	45301	ethyl 2-ethoxy-2-oxoacetate		C₆H₁₀O₄	详情	详情
(IV)	18003	4,5-dichloro-1,2-benzenediamine; 4,5-Dichloro-o-phenylenediamine; 2-amino-4,5-dichlorophenylamine	5348-42-5	C₆H₆Cl₂N₂	详情	详情
(VIII)	18007	6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione	25983-13-5	C₈H₄Cl₂N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The condensation of 4,5-dichloro-1,2-phenylenediamine (I) with diethyl oxalate (II) produced quinoxalinedione (III), which was brominated with PBr5 at 155 C to afford the dibromo derivative (IV). Displacement of one bromine group of (IV) with 4-(diethylamino)butylamine (V) furnished (VI). The remaining bromine of (VI) was then displaced with 5-(tributylstannyl)-2,2'-bithienyl (VII) to produce the title compound, isolated as the corresponding hydrochloride salt.

参考文献中间体

合成目标

【1】 Li, J.J.; Yue, W.-S.; Trivedi, B.K.; et al.; Structure-activity relationship of 2-amino-3-heteroaryl-quinoxalines as potent, non-peptide interleukine-8-receptor antagonists. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 144.

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)	18003	4,5-dichloro-1,2-benzenediamine; 4,5-Dichloro-o-phenylenediamine; 2-amino-4,5-dichlorophenylamine	5348-42-5	C₆H₆Cl₂N₂	详情	详情
(II)	17571	Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate	95-92-1	C₆H₁₀O₄	详情	详情
(III)	18007	6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione	25983-13-5	C₈H₄Cl₂N₂O₂	详情	详情
(IV)	44243	2,3-dibromo-6,7-dichloroquinoxaline		C₈H₂Br₂Cl₂N₂	详情	详情
(V)	44244	N-(4-aminobutyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,4-butanediamine		C₈H₂₀N₂	详情	详情
(VI)	44245	N-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N-[4-(diethylamino)butyl]amine; N(1)-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N(4),N(4)-diethyl-1,4-butanediamine		C₁₆H₂₁BrCl₂N₄	详情	详情
(VII)	44246			C₂₀H₃₂S₂Sn	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

The condensation of 4,5-dichloro-1,2-phenylenediamine (I) with diethyl oxalate (II) produced quinoxalinedione (III), which was brominated with PBr5 at 155 C to afford the dibromo derivative (IV). Displacement of one bromine group of (IV) with 4-(diethylamino)butylamine (V) furnished (VI). The remaining bromine of (VI) was then displaced with 2-(tributylstannyl)benzofuran (VII) to produce the title compound.

参考文献中间体

合成目标

【1】 Li, J.J.; Yue, W.-S.; Trivedi, B.K.; et al.; Structure-activity relationship of 2-amino-3-heteroaryl-quinoxalines as potent, non-peptide interleukine-8-receptor antagonists. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 144.

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)	18003	4,5-dichloro-1,2-benzenediamine; 4,5-Dichloro-o-phenylenediamine; 2-amino-4,5-dichlorophenylamine	5348-42-5	C₆H₆Cl₂N₂	详情	详情
(II)	17571	Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate	95-92-1	C₆H₁₀O₄	详情	详情
(III)	18007	6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione	25983-13-5	C₈H₄Cl₂N₂O₂	详情	详情
(IV)	44243	2,3-dibromo-6,7-dichloroquinoxaline		C₈H₂Br₂Cl₂N₂	详情	详情
(V)	44244	N-(4-aminobutyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,4-butanediamine		C₈H₂₀N₂	详情	详情
(VI)	44245	N-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N-[4-(diethylamino)butyl]amine; N(1)-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N(4),N(4)-diethyl-1,4-butanediamine		C₁₆H₂₁BrCl₂N₄	详情	详情
(VII)	44247	1-benzofuran-2-yl(tributyl)stannane		C₂₀H₃₂OSn	详情	详情

Extended Information