N(1)-(5-bromo-2-pyridinyl)-N(1)-(3,4-dichlorobenzyl)-1,3-propanediamine; N-(3-aminopropyl)-N-(5-bromo-2-pyridinyl)-N-(3,4-dichlorobenzyl)amine -Drug Synthesis Database

【结构式】

【分子编号】19334

【品名】N(1)-(5-bromo-2-pyridinyl)-N(1)-(3,4-dichlorobenzyl)-1,3-propanediamine; N-(3-aminopropyl)-N-(5-bromo-2-pyridinyl)-N-(3,4-dichlorobenzyl)amine

【CA登记号】

【分子式】C₁₅H₁₆BrCl₂N₃

【分子量】389.12166

【元素组成】C 46.3% H 4.14% Br 20.53% Cl 18.22% N 10.8%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

Reaction of 2,5-dibromopyridine (I) with an excess of 1,3-diaminopropane (II) in refluxing pyridine provided N-1-(2-pyridyl)propanediamine (III). This compound was further alkylated at the 1N with 3,4-dichlorobenzyl chloride (IV) in DMSO using NaH as the base to afford (V). From this, isothiocyanate (VI) was prepared by reaction with CS2 and DCC in THF. Subsequent coupling with trityl-protected amine (VII) yielded the thiourea (VIII). Finally, the trityl protecting group was removed by refluxing in 1 N HCl.

参考文献中间体

合成目标

【1】 Liu, S.; Tang, C.; Ho, B.; Ankersen, M.; Stidsen, C.E.; Crider, A.M.; Nonpeptide somatostatin agonists with sst4 selectivity: Synthesis and structure-activity relationships of thioureas. J Med Chem 1998, 41, 24, 4693.

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)	19330	2,5-dibromopyridine	624-28-2	C₅H₃Br₂N	详情	详情
(II)	19331	3-aminopropylamine; 1,3-propanediamine	109-76-2	C₃H₁₀N₂	详情	详情
(III)	19332	N-(3-aminopropyl)-N-(5-bromo-2-pyridinyl)amine; N(1)-(5-bromo-2-pyridinyl)-1,3-propanediamine		C₈H₁₂BrN₃	详情	详情
(IV)	19333	1,2-dichloro-4-(chloromethyl)benzene	102-47-6	C₇H₅Cl₃	详情	详情
(V)	19334	N(1)-(5-bromo-2-pyridinyl)-N(1)-(3,4-dichlorobenzyl)-1,3-propanediamine; N-(3-aminopropyl)-N-(5-bromo-2-pyridinyl)-N-(3,4-dichlorobenzyl)amine		C₁₅H₁₆BrCl₂N₃	详情	详情
(VI)	19335	N-(5-bromo-2-pyridinyl)-N-(3,4-dichlorobenzyl)-N-(3-isothiocyanatopropyl)amine; 5-bromo-N-(3,4-dichlorobenzyl)-N-(3-isothiocyanatopropyl)-2-pyridinamine		C₁₆H₁₄BrCl₂N₃S	详情	详情
(VII)	19336	3-(1-trityl-1H-imidazol-4-yl)-1-propanamine; 3-(1-trityl-1H-imidazol-4-yl)propylamine		C₂₅H₂₅N₃	详情	详情
(VIII)	19337	N-[3-[(5-bromo-2-pyridinyl)(3,4-dichlorobenzyl)amino]propyl]-N'-[3-(1-trityl-1H-imidazol-4-yl)propyl]thiourea		C₄₁H₃₉BrCl₂N₆S	详情	详情

Extended Information