3-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile -Drug Synthesis Database

【结构式】

【分子编号】11288

【品名】3-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile

【CA登记号】

【分子式】C₈H₈N₂O

【分子量】148.1644

【元素组成】C 64.85% H 5.44% N 18.91% O 10.8%

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 synthesis of [14C]-labeled prinomide has been described: The carboxylation of 1-methylpyrrole (I) with 14CO2 and butyllithium in THF gives labeled 1-methylpyrrole-2-carboxylic acid (II), which is esterified with diazomethane to the methyl ester (III). The reaction of (III) with acetonitrile by means of NaH in DMF affords 3-(1-methylpyrrol-2-yl)-3-oxopropanenitrile (IV) labeled in the carbonyl group. Finally, this compound is condensed with phenylisocyanate (V) by means of triethylamine in toluene, affording the prinomide labeled in the carbonyl group. The condensation of unlabeled (IV) with (V) labeled in the phenyl ring yields the corresponding prinomide labeled in the aromatic ring.

参考文献中间体

合成目标

【1】 Chaudhuri, N.K.; Markus, B.; Synthesis of two 14C-labeled forms of prinomide, a potential anti-inflammatory compound and its hydroxy metabolite, labeled with 14C. J Label Compd Radiopharm 1990, 28, 3, 321.

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)	11285	1-Methyl-1H-pyrrole; Methylpyrrole	96-54-8	C₅H₇N	详情	详情
(II)	11286	1-Methyl-1H-pyrrole-2-carboxylic acid; 1-Methyl-2-pyrrolecarboxylic acid	6973-60-0	C₆H₇NO₂	详情	详情
(II)	45058	1-methyl-1H-pyrrole-2-carboxylic acid		C₆H₇NO₂	详情	详情
(III)	11287	methyl 1-methyl-1H-pyrrole-2-carboxylate	37619-24-2	C₇H₉NO₂	详情	详情
(III)	45059	methyl 1-methyl-1H-pyrrole-2-carboxylate		C₇H₉NO₂	详情	详情
(IV)	11288	3-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile		C₈H₈N₂O	详情	详情
(IV)	45060	3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile		C₈H₈N₂O	详情	详情
(V)	11289	1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate	103-71-9	C₇H₅NO	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 esterification of N-methylpyrrol-2-carboxylic acid (I) with NaH and methyl iodide in DMF gives methyl N methylpyrrol 2 carboxylate (II), which is condensed with acetonitrile by means of NaH in DMF yielding 3-(1-methyl-2-pyrrolyl)-3-oxopropionitrile (III). The reaction of (III) with phenylisocyanate (IV) by means of triethylamine in toluene affords 2-cyano-3-(1-methyl-2-pyrrolyl)-3-oxo-N-phenylpropionamide (V), which is finally treated with triethanolamine (VI) in hot ethanol.

参考文献中间体

合成目标

【1】 Walker, G.N. (Novartis AG); alpha-Carbamoyl-pyrrolpropionitriles, process fortheir preparation and pharmaceutical preparations containing them. EP 0143142 .
【2】 Serradell, M.N.; Castaner, J.; Castaner, R.M.; Prinomide Triethanolamine. Drugs Fut 1987, 12, 8, 773.

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)	11286	1-Methyl-1H-pyrrole-2-carboxylic acid; 1-Methyl-2-pyrrolecarboxylic acid	6973-60-0	C₆H₇NO₂	详情	详情
(II)	11287	methyl 1-methyl-1H-pyrrole-2-carboxylate	37619-24-2	C₇H₉NO₂	详情	详情
(III)	11288	3-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile		C₈H₈N₂O	详情	详情
(IV)	11289	1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate	103-71-9	C₇H₅NO	详情	详情
(V)	28167	2-cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxo-N-phenylpropanamide		C₁₅H₁₃N₃O₂	详情	详情
(VI)	28168	2-[bis(2-hydroxyethyl)amino]-1-ethanol	102-71-6	C₆H₁₅NO₃	详情	详情

Extended Information