Copper (I) cyanide; Cuprous cyanide -Drug Synthesis Database

【结构式】

【分子编号】56856

【品名】Copper (I) cyanide; Cuprous cyanide

【CA登记号】544-92-3

【分子式】CCuN

【分子量】89.56374

【元素组成】C 13.41% Cu 70.95% N 15.64%

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：(III)

The reaction of 2,3-dichlorobenzoic acid (I) with oxalyl chloride in dichloromethane gives the acyl chloride (II), which is condensed with labeled copper cyanide (III) by means of KI in refluxing xylene to yield the 2,3-dichlorobenzoyl cyanide (IV). The condensation of (IV) with labeled aminoguanidine (V) by means of sulfuric acid in acetonitrile/water affords adduct (VI), which is finally cyclized by refluxing under the conditions of the preceding reaction to provide the target labeled diaminotriazine. The intermediate labeled copper cyanide (III) has been obtained by reaction of CuSO4 with labeled potassium cyanide (VII) and Na2S2O5 in hot water. The intermediate labeled aminoguanidine (V) has been obtained by methylation of thiourea (VIII) with dimethyl sulfate in boiling water to give S-methylisothiourea (IX), which is finally treated with hydrazine (X) and NaOH in water.

参考文献中间体

合成目标

【1】 Manning, C.O.; et al.; Synthesis of stable isotopically labelled versions of lamotrigine and its methylated metabolite. J Label Compd Radiopharm 2002, 45, 7, 611.

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)	24007	2,3-dichlorobenzoic acid	50-45-3	C₇H₄Cl₂O₂	详情	详情
(II)	24008	2,3-dichlorobenzoyl chloride	2905-60-4	C₇H₃Cl₃O	详情	详情
(III)	56856	Copper (I) cyanide; Cuprous cyanide	544-92-3	CCuN	详情	详情
(III)	56861	cyanocopper		CCuN	详情	详情
(IV)	24009	2-(2,3-dichlorophenyl)-2-oxoacetonitrile; 2,3-Dichlorobenzoylcyanide	77668-42-9	C₈H₃Cl₂NO	详情	详情
(IV)	56862	2-(2,3-dichlorophenyl)-2-oxoacetonitrile		C₈H₃Cl₂NO	详情	详情
(V)	56857			CH₆N₄	详情	详情
(V)	56866			CH₆N₄	详情	详情
(VI)	56858	1,2-dichloro-3-{cyano[(Z)-2-(diaminomethylene)hydrazono]methyl}benzene		C₉H₇Cl₂N₅	详情	详情
(VI)	56867	1,2-dichloro-3-{cyano[(Z)-2-(diaminomethylene)hydrazono]methyl}benzene		C₉H₇Cl₂N₅	详情	详情
(VII)	56859	Potassium cyanide	151-50-8	CKN	详情	详情
(VII)	56860	cyanopotassium		CKN	详情	详情
(VIII)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(VIII)	56863	thiourea		CH₄N₂S	详情	详情
(IX)	10272	[[Amino(imino)methyl]sulfanyl]methane	2986-19-8	C₂H₆N₂S	详情	详情
(IX)	56864	{[amino(imino)methyl]sulfanyl}methane		C₂H₆N₂S	详情	详情
(X)	27344	hydrazine	302-01-2	H₄N₂	详情	详情
(X)	56865	hydrazine		H₄N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The Friedel Crafts condensation of fumaryl chloride (I) with bromobenzene (II) gives 1,2-bis(4-bromobenzoyl)ethylene (III), which is reduced with Zn and Ac-OH to yield 1,4-bis(4-bromophenyl)butane-1,4-dione (IV). The cyclization of (IV) in refluxing Ac2O affords 2,5-bis(4-bromophenyl)furan (V) which is treated with CNCu in refluxing quinoline to provide 2,5-bis(4-cyanophenyl)furan (VI). The reaction of (VI) with HCl in ethanol gives the bis imidate (VII), which is finally treated with ammonia in ethanol to yield the target bis benzamidine.

参考文献中间体

合成目标

【1】 Dann, O.; et al.; Trypanocidal diamidines with three isolated ring systems. Liebigs Ann Chem 1975, 1, 160.
【2】 Das, B.P.; Boykin, D.W.; Synthesis and antiprotozoal activity of 2,5-bis (4-guanylphenyl) furans. J Med Chem 1977, 20, 4, 531-536.
【3】 Boykin, D.W.; et al.; 2,5-Bis[4-(N-alkylamidino)phenyl]furans as anti-Pneumocystis carinii agents. J Med Chem 1998, 41, 1, 124.
【4】 Boykin, D.W.; et al.; Anti-pneumocystis activity of bis-amidoximes and bis-O-alkylamidoximes prodrugs. Bioorg Med Chem Lett 1996, 6, 24, 3017.
【5】 Niigata, K.; Murakami, M.; Kagami, S.; Fujikura, S.; Kojima, A.; Tachikawa, S.; Nozaki, J.; Takahashi, K. (Yamanouchi Pharmaceutical Co., Ltd.); Novel indene derivs. or their salts. JP 1977111580 .

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)	57909	Fumaryl chloride	627-63-4	C₄H₂Cl₂O₂	详情	详情
(II)	13365	Monobromobenzene; 1-Bromobenzene；Phenylbromide;bromobenzene	108-86-1	C₆H₅Br	详情	详情
(III)	57910	(E)-1,4-bis(4-bromophenyl)-2-butene-1,4-dione		C₁₆H₁₀Br₂O₂	详情	详情
(IV)	35811	1,4-bis(4-bromophenyl)-1,4-butanedione		C₁₆H₁₂Br₂O₂	详情	详情
(V)	35812	2,5-bis(4-bromophenyl)furan		C₁₆H₁₀Br₂O	详情	详情
(VI)	56856	Copper (I) cyanide; Cuprous cyanide	544-92-3	CCuN	详情	详情
(VII)	35814	4-[5-(4-cyanophenyl)-2-furyl]benzonitrile		C₁₈H₁₀N₂O	详情	详情
(VIII)	35815	ethyl 4-(5-[4-[ethoxy(imino)methyl]phenyl]-2-furyl)benzenecarboximidoate		C₂₂H₂₂N₂O₃	详情	详情

Extended Information