2,3-dibromo-6,7-dichloroquinoxaline -Drug Synthesis Database

【结构式】

【分子编号】44243

【品名】2,3-dibromo-6,7-dichloroquinoxaline

【CA登记号】

【分子式】C₈H₂Br₂Cl₂N₂

【分子量】356.83076

【元素组成】C 26.93% H 0.56% Br 44.79% Cl 19.87% N 7.85%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

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2

该中间体在本合成路线中的序号：(IV)

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