1,1'-Carbonyldiimidazole → N-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

HRID 248989Notes

Reaction equation

HRID 248989 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.[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29].[N:40]1([CH2:46][C:47]2[CH:48]=[C:49]([CH:55]=[CH:56][CH:57]=2)[O:50][CH2:51][CH2:52][CH2:53][NH2:54])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>>[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:28]([NH:54][CH2:53][CH2:52][CH2:51][O:50][C:49]2[CH:55]=[CH:56][CH:57]=[C:47]([CH2:46][N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[CH:48]=2)=[O:29])[CH3:25])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 19762600N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine

Product 1

HCID 19762612N-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

Procedure

Preparation is effected analogously to Example 63, using 0.58 g (1.5 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine and the equimolar amounts of 1,1'-carbonyldiimidazole and 3-[3-(piperidinomethyl)phenoxy]propylamine as starting materials. Working up by chromatography analogously to Example 63 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=645 ([M+H]+, 8), 121 (100); IR (KBr): 1635 cm-1 (C=O). For further analysis, a portion of the compound is converted into the tartaric acid salt in an ethanol/ether solvent mixture; m.p.: 75° C. (ethanol/ether).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 63 yields the
  3. custompurified title compound in the form of a viscous oil

Sources & evidence

ORD record
ord-aca6bda7f8664ce7bb041b7b71445d52
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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