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【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

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.

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.

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.

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