2-amino-1,1-dimethylethylamine; 2-methyl-1,2-propanediamine -Drug Synthesis Database

【结构式】

【分子编号】29645

【品名】2-amino-1,1-dimethylethylamine; 2-methyl-1,2-propanediamine

【CA登记号】811-93-8

【分子式】C₄H₁₂N₂

【分子量】88.15276

【元素组成】C 54.5% H 13.72% N 31.78%

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：(I)

The condensation in DMF of 1,1-dimethyl-2-[(aminocarbonyl)amino]ethylamine (III) [prepared from 1,2-diamino-2-methylpropane (I) and urea (II)] and 2,3-epoxypropyl o-fluorobenzoate (VI) [prepared from o-fluorobenzoyl chloride (VI) and glycidol (V) in diethyl ether using triethylamine as a proton scavenger], followed by salt formation using 98% sulfuric acid in ethanol yields ACC-9089.

参考文献中间体

合成目标

【1】 Mai, K.X.; Kam, S.T.; Matier, W.L.; O'Donnel, J.P.; Sum, C.Y.; Gorczynski, R.J.; Lee, R.J.; Stamfli, H.F.; Barcelon-Yang, C.; Anderson, W.G.; Borgman, R.J.; [(Arylcarbonyl)oxy]propanolamines. 1. Novel beta-blockers with ultrashort duration of action. J Med Chem 1984, 27, 8, 1007.
【2】 Day, B.W.; Pento, J.T.; ACC-9089. Drugs Fut 1985, 10, 6, 447.

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)	29645	2-amino-1,1-dimethylethylamine; 2-methyl-1,2-propanediamine	811-93-8	C₄H₁₂N₂	详情	详情
(II)	19310	urea	57-13-6	CH₄N₂O	详情	详情
(III)	29646	N-(2-amino-2-methylpropyl)urea		C₅H₁₃N₃O	详情	详情
(IV)	19551	2-Fluorobenzoyl chloride	393-52-2	C₇H₄ClFO	详情	详情
(V)	29648	2-oxiranylmethanol	556-52-5	C₃H₆O₂	详情	详情
(VI)	29647	2-oxiranylmethyl 2-fluorobenzoate		C₁₀H₉FO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The cyclization of 2,2,5,5-tetramethyl-3,4-dithiahexane-1,6-dial (I) with 2-methylpropane-1,2-diamine (II) in hoot ethanol gives 3,3,6,6,10,10-hexamethyl-1,2-dithia-5,8-diazacyclodeca-4,8-diene (III), which is reduced with NaBH3CN in ethanol to afford the corresponding cyclodecane compound (IV). The condensation of (IV) with 4-(bromomethyl)benzoic acid methyl ester (V) by means of K2CO3 in refluxing acetonitrile yields the adduct (VI), which is condensed with 2-(diethylamino)ethylamine (VII) by means of Al(CH3)3 in refluxing dichloromethane to provide the corresponding amide (VIII). Ring opening of (VIII) at the S-S bond by means of dithiothreitol (DTT) and TEA in MeOH gives the dithiol (IX), which is finally treated with TcO4Na, SnCl2 and NaOH in ethanol/water.

参考文献中间体

合成目标

【1】 Auzeloux, P.; et al.; Technetium-99m radiolabelling of an N-amino-alkyl-benzamide nitrido- and oxo-technetium bis(aminoethanethiol) derivative synthesis and biological results. Potential melanoma tracer agents. J Label Compd Radiopharm 1999, 42, 6, 567.

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)	38370	2-[(1,1-dimethyl-2-oxoethyl)disulfanyl]-2-methylpropanal		C₈H₁₄O₂S₂	详情	详情
(II)	29645	2-amino-1,1-dimethylethylamine; 2-methyl-1,2-propanediamine	811-93-8	C₄H₁₂N₂	详情	详情
(III)	38371	3,3,6,6,10,10-hexamethyl-3,6,7,10-tetrahydro-1,2,5,8-dithiadiazecine		C₁₂H₂₂N₂S₂	详情	详情
(IV)	38372	3,3,6,6,10,10-hexamethyl-1,2,5,8-dithiadiazecane		C₁₂H₂₆N₂S₂	详情	详情
(V)	14565	methyl 4-(bromomethyl)benzoate	2417-72-3	C₉H₉BrO₂	详情	详情
(VI)	38373	methyl 4-[(3,3,7,7,10,10-hexamethyl-1,2,5,8-dithiadiazecan-5-yl)methyl]benzoate		C₂₁H₃₄N₂O₂S₂	详情	详情
(VII)	12420	N-(2-Aminoethyl)-N,N-diethylamine; N,N-Diethylethylene-diamine; N(1),N(1)-Diethyl-1,2-ethanediamine	100-36-7	C₆H₁₆N₂	详情	详情
(VIII)	38374	N-[2-(diethylamino)ethyl]-4-[(3,3,7,7,10,10-hexamethyl-1,2,5,8-dithiadiazecan-5-yl)methyl]benzamide		C₂₆H₄₆N₄OS₂	详情	详情
(IX)	38375	N-[2-(diethylamino)ethyl]-4-[[[2-methyl-2-[(2-methyl-2-sulfanylpropyl)amino]propyl](2-methyl-2-sulfanylpropyl)amino]methyl]benzamide		C₂₆H₄₈N₄OS₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

The cyclization of 2,2,5,5-tetramethyl-3,4-dithiahexane-1,6-dial (I) with 2-methylpropane-1,2-diamine (II) in hot ethanol gives 3,3,6,6,10,10-hexamethyl-1,2-dithia-5,8-diazacyclodeca-4,8-diene (III), which is reduced with NaBH3CN in ethanol to afford the corresponding cyclodecane compound (IV). The condensation of (IV) with 4-(bromomethyl)benzoic acid methyl ester (V) by means of K2CO3 in refluxing acetonitrile yields the adduct (VI), which is condensed with 2-(diethylamino)ethylamine (VII) by means of Al(CH3)3 in refluxing dichloromethane to provide the corresponding amide (VIII). Ring opening of (VIII) at the S-S bond by means of dithiothreitol (DTT) and TEA in methanol gives the dithiol (IX), which is finally treated with TcO4Na, PPh3 and N,S-dimethyldithiocarbazate (MDTCZ) in ethanol / 1M HCl.

参考文献中间体

合成目标

【1】 Auzeloux, P.; et al.; Technetium-99m radiolabelling of an N-amino-alkyl-benzamide nitrido- and oxo-technetium bis(aminoethanethiol) derivative synthesis and biological results. Potential melanoma tracer agents. J Label Compd Radiopharm 1999, 42, 6, 567.

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)	38370	2-[(1,1-dimethyl-2-oxoethyl)disulfanyl]-2-methylpropanal		C₈H₁₄O₂S₂	详情	详情
(II)	29645	2-amino-1,1-dimethylethylamine; 2-methyl-1,2-propanediamine	811-93-8	C₄H₁₂N₂	详情	详情
(III)	38371	3,3,6,6,10,10-hexamethyl-3,6,7,10-tetrahydro-1,2,5,8-dithiadiazecine		C₁₂H₂₂N₂S₂	详情	详情
(IV)	38372	3,3,6,6,10,10-hexamethyl-1,2,5,8-dithiadiazecane		C₁₂H₂₆N₂S₂	详情	详情
(V)	14565	methyl 4-(bromomethyl)benzoate	2417-72-3	C₉H₉BrO₂	详情	详情
(VI)	38373	methyl 4-[(3,3,7,7,10,10-hexamethyl-1,2,5,8-dithiadiazecan-5-yl)methyl]benzoate		C₂₁H₃₄N₂O₂S₂	详情	详情
(VII)	12420	N-(2-Aminoethyl)-N,N-diethylamine; N,N-Diethylethylene-diamine; N(1),N(1)-Diethyl-1,2-ethanediamine	100-36-7	C₆H₁₆N₂	详情	详情
(VIII)	38374	N-[2-(diethylamino)ethyl]-4-[(3,3,7,7,10,10-hexamethyl-1,2,5,8-dithiadiazecan-5-yl)methyl]benzamide		C₂₆H₄₆N₄OS₂	详情	详情
(IX)	38375	N-[2-(diethylamino)ethyl]-4-[[[2-methyl-2-[(2-methyl-2-sulfanylpropyl)amino]propyl](2-methyl-2-sulfanylpropyl)amino]methyl]benzamide		C₂₆H₄₈N₄OS₂	详情	详情

Extended Information