1,1'-Carbonyldiimidazole → N-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-N'-[3-[N-[3-phenyl-3-(2-pyridyl)propyl]-N-methylamino]propyl]urea

HRID 248973Notes

Reaction equation

HRID 248973 reaction equation
[CH3:1][N:2]([CH2:7][CH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:3][CH2:4][CH2:5][NH2:6].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[NH:34]([C:38]1[S:39][CH:40]=[C:41]([CH2:43][S:44][CH2:45][CH2:46][NH2:47])[N:42]=1)[C:35]([NH2:37])=[NH:36]>C(OCC)(=O)C.CO>[NH:34]([C:38]1[S:39][CH:40]=[C:41]([CH2:43][S:44][CH2:45][CH2:46][NH:47][C:22]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH2:7][CH2:8][CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH3:1])=[O:23])[N:42]=1)[C:35]([NH2:37])=[NH:36]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762511HCID 19762511, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483843N-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-N'-[3-[N-[3-phenyl-3-(2-pyridyl)propyl]-N-methylamino]propyl]urea

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.85 g (3 mmol) of N-methyl-N-[3-phenyl-3-(2-pyridyl)propyl]-1,3-propanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.75 g (3.2 mmol) of 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine as starting materials. Working up by chromatography (eluant: chloroform/methanol 9+1) analogously to Example 63 yields the purified title compound in the form of an oil; MS (+FAB method): m/z (rel. int. [%])=541 ([M+H]+, 2), 196 (100); IR (KBr): 1650 cm-1 (C=O). For analytical purposes a sample is converted into the maleic acid salt and recrystallised from ether/ethanol; m.p.: 95°-98° C.

Workup

  1. customPreparation
  2. custompurified title compound in the form of an oil
  3. customrecrystallised from ether/ethanol

Sources & evidence

ORD record
ord-aa5c5d116bd04ad6a6034ba5c4a066a4
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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