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【结 构 式】

【分子编号】38371

【品名】3,3,6,6,10,10-hexamethyl-3,6,7,10-tetrahydro-1,2,5,8-dithiadiazecine

【CA登记号】

【 分 子 式 】C12H22N2S2

【 分 子 量 】258.45216

【元素组成】C 55.77% H 8.58% N 10.84% S 24.81%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

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.

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2

该中间体在本合成路线中的序号:(III)

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.

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