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

HRID 248967Notes

Reaction equation

HRID 248967 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:9][CH2:10][N:11]([CH3:16])[CH2:12][CH2:13][CH2:14][NH2:15])=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].[NH:35]([C:39]1[S:40][CH:41]=[C:42]([CH2:44][S:45][CH2:46][CH2:47][NH2:48])[N:43]=1)[C:36]([NH2:38])=[NH:37]>C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][NH:15][C:23]([NH:48][CH2:47][CH2:46][S:45][CH2:44][C:42]2[N:43]=[C:39]([NH:35][C:36]([NH2:38])=[NH:37])[S:40][CH:41]=2)=[O:24])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762536HCID 19762536, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483844N-[3-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]propyl]-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]urea

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.9 g (2.8 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,3-propanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.73 g (3.1 mmol) of 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine as starting materials. Working up by chromatography (eluant: ethyl acetate/methanol 85+15) analogously to Example 63 yields the purified title compound in the form of a dry foam; MS (+FAB method): m/z (rel. int.[%])=575 ([M+H]+, 3), 155 (22), 230 (100); IR (KBr): 1646 cm-1 (C=O).

Workup

  1. customPreparation
  2. custompurified title compound in the form of a dry foam

Sources & evidence

ORD record
ord-fb5ea7fca4c141238f69eaaf692f6037
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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