dicyclopropylmethanamine -Drug Synthesis Database

【结构式】

【分子编号】24691

【品名】dicyclopropylmethanamine

【CA登记号】

【分子式】C₇H₁₃N

【分子量】111.18696

【元素组成】C 75.62% H 11.78% N 12.6%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(II)

The addition of dicyclopropylmethylamine (II) to B-chloroethyl isocyanate (I) in THF gives N-(dicyclopropylmethyl)-N'-(Beta-chloroethyl)urea (III), which is then cyclized in refluxing water.

参考文献中间体

合成目标

【1】 Malen, C.; Desnos, M.; Laubie, M.; Poignant, J.C. (Servier Laboratoires); Cyclopropylamines as pharmaceuticals. DE 2362754; ES 421879; FR 2212143; GB 1453703; JP 50004084; JP 53056664; JP 53056665 .
【2】 Castaner, J.; Prous, J.; S-3341. Drugs Fut 1986, 11, 6, 470.

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)	11237	1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate	1943-83-5	C₃H₄ClNO	详情	详情
(II)	24691	dicyclopropylmethanamine		C₇H₁₃N	详情	详情
(III)	24692	N-(chloromethyl)-N'-(dicyclopropylmethyl)urea		C₉H₁₅ClN₂O	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 title compound was prepared by two related procedures. Treatment of cis-4,5-dimethyl-2-pyrrolidinone (I) with dimethyl sulfate gave the methoxypyrroline (II). The methoxy group of (II) was then displaced with dicyclopropylmethylamine (III) to provide the desired aminopyrroline.

参考文献中间体

合成目标

【1】 Renard, P.; Feldman, J.; Bousquet, P.; Bruban, V.; Schann, S.; Scalbert, E.; Pfeiffer, B.; Ehrhardt, J.-D. (ADIR et Cie.); Aminopyrrolidine derivs., processes for their preparation and pharmaceutical compsns. comprising them. EP 1101756; FR 2801051; JP 2001139545; US 6300366 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	51174	4,5-dimethyl-2-pyrrolidinone	C₆H₁₁NO	详情	详情
(II)	51175	5-methoxy-2,3-dimethyl-3,4-dihydro-2H-pyrrole; 2,3-dimethyl-3,4-dihydro-2H-pyrrol-5-yl methyl ether	C₇H₁₃NO	详情	详情
(III)	24691	dicyclopropylmethanamine	C₇H₁₃N	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

In a more convenient method, pyrrolidinone (I) was converted to the thiolactam (IV) upon treatment with Lawesson's reagent. Alkylation of (IV) with iodomethane furnished the corresponding (S)-methyl derivative (V). This was finally condensed with dicyclopropylmethylamine (III), yielding the title compound.

参考文献中间体

合成目标

【1】 Feldman, J.; Bousquet, P.; Pfeiffer, B.; Bruban, V.; Scalbert, E.; Renard, P.; Pompermayer, K.; Schann, S.; Ehrhardt, J.-D.; Synthesis and biological evaluation of pyrrolinic isosteres of rilmenidine. Discovery of cis-I-trans-dicyclopropylmethyl-(4,5-dimethyl-4,5-dihydro-3H-pyrrol-2-yl)-amine (LNP 509), an I1 imidazoline receptor selective ligand with hypotensive activity. J Med Chem 2001, 44, 10, 1588.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	51174	4,5-dimethyl-2-pyrrolidinone	C₆H₁₁NO	详情	详情
(III)	24691	dicyclopropylmethanamine	C₇H₁₃N	详情	详情
(IV)	51176	4,5-dimethyl-2-pyrrolidinethione	C₆H₁₁NS	详情	详情
(V)	51177	2,3-dimethyl-3,4-dihydro-2H-pyrrol-5-yl methyl sulfide; 2,3-dimethyl-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole	C₇H₁₃NS	详情	详情

Extended Information