1,1'-Carbonyldiimidazole → N-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-N'-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]urea

HRID 249011Notes

Reaction equation

HRID 249011 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].[NH:40]([C:44]1[S:45][CH:46]=[C:47]([CH2:49][S:50][CH2:51][CH2:52][NH2:53])[N:48]=1)[C:41]([NH2:43])=[NH:42]>>[NH:40]([C:44]1[S:45][CH:46]=[C:47]([CH2:49][S:50][CH2:51][CH2:52][NH:53][C:28]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:8]([CH2:7][C:6]2[CH:26]=[CH:27][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH3:25])=[O:29])[N:48]=1)[C:41]([NH2:43])=[NH:42]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762600N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamineHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178491101N-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-N'-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]urea

Procedure

Preparation is effected analogously to Example 63, using 0.74 g (2.0 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 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine 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. [%])=628 ([M+H]+, 4), 121 (100); IR (KBr): 1597 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.: 60° 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-f0f9ae9e10d84d14a27633c44acc705a
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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