N-(3-aminopropyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,3-propanediamine -Drug Synthesis Database

【结构式】

【分子编号】29977

【品名】N-(3-aminopropyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,3-propanediamine

【CA登记号】104-78-9

【分子式】C₇H₁₈N₂

【分子量】130.2334

【元素组成】C 64.56% H 13.93% N 21.51%

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：(XV)

Compound (X) is reduced with H2 over Pd/C in acetic acid to 1-hydroxy-5-methyl-6-[(3-amino-4-pyridyl)amino]isoquinolin (Xl). The treatment of (XI) with NaNO2 in acetic acid yields 1-(1-hydroxy-5-methyl-6-isoquinolyl)triazolo[4,5-c]pyridine (XII), which is converted into 1-hydroxy-5-methyldipyrido[4,3-b][3,4-f]indole (XIII). The reaction of (XIII) with PCl5 in refluxing POCl3 gives 1-chloro-5-methyldipyrido[4,3-b][3,4-f]indole (XIV), which is finally condensed with 3-(diethylamino)propylamine (XV) by heating at 150 C.

参考文献中间体

合成目标

【1】 Rivalle, C.; Lhoste, J.M.; Bisagni, E.; Duerocq, C.; Synthesis of 10-substituted 5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinolines. J Chem Soc - Perkins Trans I 1979, 142-145.
【2】 Van der Burg, W.J. (Akzo Nobel N.V.); Tetracyclic compounds. BE 0840362; CH 622261; DE 2614406; DK 142498; ES 446634; FR 2305986; GB 1543171; JP 76122099; NL 754075 .
【3】 Hopkins, S.J.; Serradell, M.N.; Castaner, J.; BD-40. Drugs Fut 1984, 9, 2, 96.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	29972	5-methyl-6-[(3-nitro-4-pyridinyl)amino]-1-isoquinolinol		C₁₅H₁₂N₄O₃	详情	详情
(XI)	29973	6-[(3-amino-4-pyridinyl)amino]-5-methyl-1-isoquinolinol		C₁₅H₁₄N₄O	详情	详情
(XII)	29974	5-methyl-6-(1H-[1,2,3]triazolo[4,5-c]pyridin-1-yl)-1-isoquinolinol		C₁₅H₁₁N₅O	详情	详情
(XIII)	29975	6-methyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinolin-10-ol		C₁₅H₁₁N₃O	详情	详情
(XIV)	29976	10-chloro-6-methyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinoline		C₁₅H₁₀ClN₃	详情	详情
(XV)	29977	N-(3-aminopropyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,3-propanediamine	104-78-9	C₇H₁₈N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XV)

1-hydroxy-5-methyl-6-[(3-nitro-4-pyridyl)amino]isoquinoline (X) is heated with phosphorous chloride oxide to give 1-chloro-5-methyl-6-[(3-nitro-4-pyridyl)amino]isoquinoline (XVI), which is reduced with H2 over Raney-Ni giving 6-[(3-amino-4-pyridyl)amino]-1-chloro-5-methylisoquinoline (XVII). This compound is treated with sodium nitrite to give 1-(1-chloro-5-methyl-6-isoquinolyl)triazolo[4,5-c]pyridine (XVIII), which is cyclized to 1-chloro-5-methylpyrido[4,3-b][3,4-f]indole (XIV), which is finally condensed with 3-(diethylamino)propylamine (XV) by heating at 150 C.

参考文献中间体

合成目标

【1】 Rivalle, C.; Lhoste, J.M.; Bisagni, E.; Duerocq, C.; Synthesis of 10-substituted 5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinolines. J Chem Soc - Perkins Trans I 1979, 142-145.
【2】 Hopkins, S.J.; Serradell, M.N.; Castaner, J.; BD-40. Drugs Fut 1984, 9, 2, 96.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	29972	5-methyl-6-[(3-nitro-4-pyridinyl)amino]-1-isoquinolinol		C₁₅H₁₂N₄O₃	详情	详情
(XIV)	29976	10-chloro-6-methyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinoline		C₁₅H₁₀ClN₃	详情	详情
(XV)	29977	N-(3-aminopropyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,3-propanediamine	104-78-9	C₇H₁₈N₂	详情	详情
(XVI)	29978	N-(1-chloro-5-methyl-6-isoquinolinyl)-N-(3-nitro-4-pyridinyl)amine; 1-chloro-5-methyl-N-(3-nitro-4-pyridinyl)-6-isoquinolinamine		C₁₅H₁₁ClN₄O₂	详情	详情
(XVII)	29979	N-(3-amino-4-pyridinyl)-N-(1-chloro-5-methyl-6-isoquinolinyl)amine; N(4)-(1-chloro-5-methyl-6-isoquinolinyl)-3,4-pyridinediamine		C₁₅H₁₃ClN₄	详情	详情
(XVIII)	29980	1-chloro-5-methyl-6-(1H-[1,2,3]triazolo[4,5-c]pyridin-1-yl)isoquinoline		C₁₅H₁₀ClN₅	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VI)

Condensation of 4-methoxybenzaldehyde (I) with gamma-butyrolactone (II) by means of NaOMe yields furanone derivative (III), which is then reduced in ether with LiAlH4 to afford diol (IV). Mesylation of (IV) by means of MsCl and Et3N in benzene provides dimesylate (V), which is finally condensed with amine (VI) with simultaneous cyclization in refluxing benzene.

参考文献中间体

合成目标

【1】 Batra, S.; et al.; A new class of potential chloroquine-resistance reversal agents for plasmodia: Syntheses and biological evaluation of 1-(3'-diethylaminopropyl)-3-(substituted phenylmethylene)pyrrolidines. J Med Chem 2000, 43, 18, 3428.

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)	27251	4-methoxybenzaldehyde; Anisicaldehyde; p-anisaldehyde	123-11-5	C₈H₈O₂	详情	详情
(II)	44219	1,2-dioxolan-3-one		C₃H₄O₃	详情	详情
(III)	44220	4-[(E)-(4-methoxyphenyl)methylidene]-1,2-dioxolan-3-one		C₁₁H₁₀O₄	详情	详情
(IV)	44221	2-[(E)-(4-methoxyphenyl)methylidene]-1,4-butanediol		C₁₂H₁₆O₃	详情	详情
(V)	44222	5-[(E)-(4-methoxyphenyl)methylidene]-2,9-dimethyl-2,9-dimethylene-3,8-dioxa-2lambda(6),9lambda(6)-dithia-1,9-decadiene; methyl 4-[(E)-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-1-butenyl]phenyl ether		C₁₈H₂₈O₃S₂	详情	详情
(VI)	29977	N-(3-aminopropyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,3-propanediamine	104-78-9	C₇H₁₈N₂	详情	详情

Extended Information