N-(2-Hydroxyethyl)nicotinamide -Drug Synthesis Database

【结构式】

【分子编号】13982

【品名】N-(2-Hydroxyethyl)nicotinamide

【CA登记号】

【分子式】C₈H₁₀N₂O₂

【分子量】166.17968

【元素组成】C 57.82% H 6.07% N 16.86% O 19.26%

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 esteritication of nicotinic acid (I) with methanol and HCl or H2SO4 yields the corresponding methyl ester (II), which is treated with ethanolamine (A) to afford N-(beta-hydroxyethyl)nicotinamide (III). Finally, this compound is transformed into the nitrate ester by the usual methods.

参考文献中间体

合成目标

【1】 Masayoshi, S.; Solubilizing agents. V. Pyridinecarboxamides. Yakugaku Zasshi 1960, 80, 1706-12.
【2】 Thorpe, P.J.; Castaner, J.; SG-75. Drugs Fut 1979, 4, 2, 134.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(I)	10752	Nicotinic acid; Niacin	59-67-6	C₆H₅NO₂	详情	详情
(II)	13980	methyl nicotinate; Nicotinic acid, methyl ester	93-60-7	C₇H₇NO₂	详情	详情
(III)	13982	N-(2-Hydroxyethyl)nicotinamide		C₈H₁₀N₂O₂	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 starting products are prepared as follows: The reaction of pyridine-3-carboxylic acid methyl ester (I) with ethanolamine (II) gives the 2-hydroxyethylamide (III), which by reaction with diketene in THF yields the corresponding acetoacetic ester (V). The reaction of (V) with ammonia in THF affords the expected 3-aminocrotonate ester (VI).

参考文献中间体

合成目标

【1】 Ogawa, T.; Hatayama, K.; Maeda, H.; Kita, Y.; Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates. Chem Pharm Bull 1994, 42, 8, 1579-89.
【2】 Mealy, N.; Martel, A.M.; Castaner, J.; CD-832.HCl. Drugs Fut 1996, 21, 12, 1221.
【3】 Kelly, R.C.; Martin, D.G.; Aristoff, P.A. (Pharmacia Corp.); Novel CC-1065 analogs. AU 8812290; EP 0340243; WO 8804659 .

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)	13980	methyl nicotinate; Nicotinic acid, methyl ester	93-60-7	C₇H₇NO₂	详情	详情
(II)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(III)	13982	N-(2-Hydroxyethyl)nicotinamide		C₈H₁₀N₂O₂	详情	详情
(IV)	11367	4-Methylene-2-oxetanone; Acetyl ketene	674-82-8	C₄H₄O₂	详情	详情
(V)	13984	2-[(3-pyridinylcarbonyl)amino]ethyl 3-oxobutanoate		C₁₂H₁₄N₂O₄	详情	详情
(VI)	13985	2-[(3-pyridinylcarbonyl)amino]ethyl (E)-3-amino-2-butenoate		C₁₂H₁₅N₃O₃	详情	详情

Extended Information