ethyl cyanoiminoformate -Drug Synthesis Database

【结构式】

【分子编号】24747

【品名】ethyl cyanoiminoformate

【CA登记号】

【分子式】C₄H₆N₂O

【分子量】98.10452

【元素组成】C 48.97% H 6.16% N 28.55% O 16.31%

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)

This compound can be obtained through two different ways from 4-(4-aminophenyl)-1H-imidazole (I): 1) By condensation of compound (I) with ethyl N-isopropylformimidate (II) in ethanol. 2) The reaction of compound (I) with ethyl N-cyanoformimidate (III) gives N'-cyano-N-(4-1H-imidazol-4-ylphenyl)formamidine (IV), which is treated with isopropylamine (V).

参考文献中间体

合成目标

【1】 Cereda, E.; Donetti, A.; Del Soldato, P.; Bergamoschi, M.; Imidazolylphenyl amidines, pharmaceutical compositions containing same and use thereof. EP 0053407; ES 8207147; ES 8207148; ES 8207149; ES 8207150; ES 8207151; ES 8207152; GB 2088375; JP 57120575; US 4386099; US 4465841 .
【2】 Donetti, A.; et al.; (Imidazoylphenyl)formamidines. A structurally novel class of potent histamine H2-receptor antagonists. J Med Chem 1984, 27, 3, 380-386.
【3】 Serradell, M.N.; de Angelis, L.; Castaner, J.; Mifentidine. Drugs Fut 1984, 9, 11, 825.

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)	34316	4-(1H-imidazol-4-yl)phenylamine; 4-(1H-imidazol-4-yl)aniline		C₉H₉N₃	详情	详情
(II)	34317	ethyl isopropyliminoformate		C₆H₁₃NO	详情	详情
(III)	24747	ethyl cyanoiminoformate		C₄H₆N₂O	详情	详情
(IV)	34318	N-cyano-N'-[4-(1H-imidazol-4-yl)phenyl]iminoformamide		C₁₁H₉N₅	详情	详情
(V)	23933	2-Propanamine; Isopropylamine	75-31-0	C₃H₉N	详情	详情

合成路线2

该中间体在本合成路线中的序号：

The hydrolysis of 2,6-diaminopyridine (I) in 36% aqueous hydrochloric acid leads to 2-amino-6-hydroxypyridine (II), which can be converted by several ways to the final product CGP 28014. Two are described here: a) Conversion of 2-amino-6-hydroxypyridine (II) with N,N-dimethylformamide diethylacetal gives the N-(2-oxopyridin-6-yl)-N',N'-dimethylformamidine (IV), which is transaminated with dipropylamine to CGP 28014. b) Reaction of 2-amino-6-hydroxypyridine (II) with ethyl-N-cyanoformimidate (2) yields N-(2-oxopyridin-6-yl)-N'-cyanoformamidine (III), which is heated with dipropylamine to give CGP 28014.

参考文献中间体

合成目标

【1】 Donetti, A.; Bellora, E.; Cereda, E.; A new convenient synthesis of H2-aryl-H1-alkylformamidines and N2-aryl-N1,N1-dialkylformamidines. Synthesis 1986, 288-91.
【2】 Von Sprecher, G.; Waldmeier, P. (Novartis AG); Pyridine derivs. EP 0239533; JP 1987226959; US 4683938 .
【3】 Mobius, H.J.; Waldmeier, P.C.; Von Sprecher, G.; CGP 28014. Drugs Fut 1992, 17, 4, 275.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	24747	ethyl cyanoiminoformate		C₄H₆N₂O	详情	详情
(I)	12407	2,6-Pyridinediamine; 6-Amino-2-pyridinylamine; 2,6-Diaminopyridine	141-86-6	C₅H₇N₃	详情	详情
(II)	12408	6-Amino-2-pyridinol		C₅H₆N₂O	详情	详情
(III)	12409	N'-Cyano-N-(6-oxo-1,6-dihydro-2-pyridinyl)iminoformamide		C₇H₆N₄O	详情	详情
(IV)	12410	N,N-Dimethyl-N'-(6-oxo-1,6-dihydro-2-pyridinyl)iminoformamide		C₈H₁₁N₃O	详情	详情

Extended Information