3-chloro-N-(3-methoxyphenethyl)-N-methyl-1-propanamine -Drug Synthesis Database

【结构式】

【分子编号】24060

【品名】3-chloro-N-(3-methoxyphenethyl)-N-methyl-1-propanamine

【CA登记号】

【分子式】C₁₃H₂₀ClNO

【分子量】241.76064

【元素组成】C 64.59% H 8.34% Cl 14.66% N 5.79% O 6.62%

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)

By condensation of 2-(3-methoxyphenyl)tetradecanenitrile (I) [prepared by alkylation of 3-methoxyphenylacetonitrile (III) with 1-bromoundecane (IV) with 1-chloro-4-methyl-6-(3-methoxyphenyl)-4-azahexane (II) (prepared by alkylation of N-methyl-[2-(3-methoxyphenyl)ethylamine (VI) with 1-bromo-3-chloropropane (V)) by means of sodium amide in refluxing toluene.

参考文献中间体

合成目标

【1】 Ehrmann, O.; et al. (BASF AG); omega-Cyano-1, omega-diphenyl-azaalkiane derivatives, their preparation and drugs containing them. DE 3144150 .
【2】 Castaner, J.; Prous, J.; Anipamil. Drugs Fut 1986, 11, 3, 171.

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)	24059	2-(3-methoxyphenyl)tetradecanenitrile		C₂₁H₃₃NO	详情	详情
(II)	24060	3-chloro-N-(3-methoxyphenethyl)-N-methyl-1-propanamine		C₁₃H₂₀ClNO	详情	详情
(III)	24061	3-methoxyphenylacetonitrile; 2-(3-methoxyphenyl)acetonitrile	19924-43-7	C₉H₉NO	详情	详情
(IV)	24062	1-bromododecane	143-15-7	C₁₂H₂₅Br	详情	详情
(V)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(VI)	24064	2-(3-methoxyphenyl)-N-methyl-1-ethanamine		C₁₀H₁₅NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXX)

In a related semisynthetic strategy, didemnin A (XXIX) was first acylated by N-Boc-L-proline (XXXIII) yielding amide (XXXIV), which was further deprotected by treatment with HCl in EtOAc. The resultant prolyl didemnin A (XXXV) was then coupled with pyruvic acid (XXX) to furnish the title compound

参考文献中间体

合成目标

【1】 Rinehart, K.L.; Katauskas, A.J. (University of Illinois); Semi-synthetic studies toward didemnin analogues. EP 0973518; JP 2001503746; WO 9817275 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXIX)	50796	(2R)-N-[(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin-7-yl]-4-methyl-2-(methylamino)pentanamide	C₄₉H₇₈N₆O₁₂	详情	详情
(XXX)	24060	3-chloro-N-(3-methoxyphenethyl)-N-methyl-1-propanamine	C₁₃H₂₀ClNO	详情	详情
(XXXII)	16734	(2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid	C₁₀H₁₇NO₄	详情	详情
(XXXIV)	62543	tert-butyl (2S)-2-{[{(1R)-1-[({(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraaz	C₅₉H₉₃N₇O₁₅	详情	详情
(XXXV)	62544	(2S)-N-{(1R)-1-[({(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosi	C₅₄H₈₅N₇O₁₃	详情	详情

Extended Information