2-pyrrolidinecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】22654

【品名】2-pyrrolidinecarboxamide

【CA登记号】2812-47-7

【分子式】C₅H₁₀N₂O

【分子量】114.14728

【元素组成】C 52.61% H 8.83% N 24.54% O 14.02%

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：(II)

a) N-Protected L-Leucine activated as the pentafluorophenyl ester (I) is coupled with L-prolinamide (II), and the resulting dipeptide (III) is deprotected te (IV) and coupled with L-pyro-2-aminoadipic acid pentatluorophenyl ester (V) to give RGH-2202.

参考文献中间体

合成目标

【1】 Kisfaludy, L.; Szporny, L.; Pálosi, É.; Szirtes, T.; Synthesis of thyrotropin-releasing hormone analogu. J Med Chem 1986, 29, 1654.
【2】 Szirtes, T.; Szporny, L.; Pálosi, É.; Kisfaludy, L.; Synthesis of thyrotropin releasing hormone analogu. J Med Chem 1984, 27, 741.
【3】 Nogradi, M.; RGH-2202. Drugs Fut 1988, 13, 5, 420.

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)	22653	2,3,4,5,6-pentafluorophenyl 2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoate		C₂₀H₁₈F₅NO₄	详情	详情
(II)	22654	2-pyrrolidinecarboxamide	2812-47-7	C₅H₁₀N₂O	详情	详情
(III)	22655	benzyl 1-[[2-(aminocarbonyl)-1-pyrrolidinyl]carbonyl]-3-methylbutylcarbamate		C₁₉H₂₇N₃O₄	详情	详情
(IV)	22656	1-[2-(aminocarbonyl)-1-pyrrolidinyl]-4-methyl-1-oxo-2-pentanaminium chloride		C₁₁H₂₂ClN₃O₂	详情	详情
(V)	22657	2,3,4,5,6-pentafluorophenyl (2S)-6-oxo-2-piperidinecarboxylate		C₁₂H₈F₅NO₃	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 proline (I) with SOCl2 and ethanol gives ethyl prolinate (II), which by treatment with NH3 in methanol is converted into prolinamide (III). The acylation of (III) with cyclopropylcarbonyl chloride (IV) by means of K2CO3 in acetone yields 1-cyclopropylcarbonyl-2-carbamoylpyrrolidine (V), which is reduced with LiAlH4 in ether to afford 1-cyclopropylmethyl-2-aminomethylpyrrolidine (VI) (1,2). Finally this compound is condensed with ethyl 5-sulfamoyl-2-methoxybenzoate (VII) by heating at 120 C

参考文献中间体

合成目标

【1】 Kaplan, J.P.; et al. (Synthelabo, S.A.); BE 857544; DE 2735036; FR 2360572; FR 2372157; FR 2395261; GB 1555890; JP 7825563; NL 7708571; ZA 7704743 .
【2】 Kaplan, J.P.; et al. (Synthelabo, S.A.); BE 836752; CA 1039731; CH 612668; DE 2556457; FR 2294698; FR 2327771; FR 2331345; GB 1508880; JP 7748661; NL 7514620; US 4021567; US 4156060; US 4172143; US 4189495; ZA 7507828 .
【3】 (Synthelabo, S.A.); BE 861866; FR 2394529; GB 1560019; JP 7905969; NL 7713631; ZA 7706950 .
【4】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Hillier, K.; Cipropride. Drugs Fut 1981, 6, 4, 220.
【5】 Obitz, D.C.L. (Synthelabo, S.A.); FR 2393794 .

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)	61051	ethyl 2-pyrrolidinecarboxylate		C₅H₉NO₂	详情	详情
(II)	61052	ethyl 2-pyrrolidinecarboxylate		C₇H₁₃NO₂	详情	详情
(III)	22654	2-pyrrolidinecarboxamide	2812-47-7	C₅H₁₀N₂O	详情	详情
(IV)	14601	N-(2-oxo-2-phenylethyl)acetamide		C₁₀H₁₁NO₂	详情	详情
(V)	61053	1-(cyclopropylcarbonyl)-2-pyrrolidinecarboxamide		C₉H₁₄N₂O₂	详情	详情
(VI)	61054	[1-(cyclopropylmethyl)-2-pyrrolidinyl]methanamine; [1-(cyclopropylmethyl)-2-pyrrolidinyl]methylamine		C₉H₁₈N₂	详情	详情
(VII)	61055	ethyl 5-(aminosulfonyl)-2-methoxybenzoate		C₁₀H₁₃NO₅S	详情	详情

Extended Information