N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine → N-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-nitro-1,1-ethenediamine

HRID 248998Notes

Reaction equation

HRID 248998 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.CS[C:30]([NH:35][CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH:41]=1)=[CH:31][N+:32]([O-:34])=[O:33]>>[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:30]([NH:35][CH2:36][CH2:37][CH2:38][O:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)[CH:41]=2)=[CH:31][N+:32]([O-:34])=[O:33])[CH3:25])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 19762600N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamineHCID 678820931-Methylthio-1-[3-[3-(piperidinomethyl)phenoxy]propyl]amino-2-nitroethene

Product 1

HCID 67882064N-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-nitro-1,1-ethenediamine

Procedure

Preparation is effected analogously to Example 22, using 0.54 g (1.45 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine and the equimolar amount of 1-methylthio-1-[3-[3-(piperidinomethyl)phenoxy]propyl]amino-2-nitroethene as starting materials. Working up by chromatography analogously to Example 22 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=688 ([M+H]+, 5), 121 (100). For further analysis, a portion of the compound is converted into the tartaric acid salt in an ethanol/ether solvent mixture; m.p.: 73° C. (ethanol/ether).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 22 yields the
  3. custompurified title compound in the form of a viscous oil

Sources & evidence

ORD record
ord-0266f57ec9b44ef5b1b602f179830759
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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