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

HRID 248974Notes

Reaction equation

HRID 248974 reaction equation
[CH3:1][N:2]([CH2:6][CH2:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:3][CH2:4][NH2:5].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22].[NH:33]([C:37]1[S:38][CH:39]=[C:40]([CH2:42][S:43][CH2:44][CH2:45][NH2:46])[N:41]=1)[C:34]([NH2:36])=[NH:35]>C(OCC)(=O)C.CO>[NH:33]([C:37]1[S:38][CH:39]=[C:40]([CH2:42][S:43][CH2:44][CH2:45][NH:46][C:21]([NH:5][CH2:4][CH2:3][N:2]([CH2:6][CH2:7][CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH3:1])=[O:22])[N:41]=1)[C:34]([NH2:36])=[NH:35]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762593HCID 19762593, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178484353N-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-N'-[2-[N-[3-phenyl-3-(2-pyridyl)propyl]-N-methylamino]ethyl]urea

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 1 g (3.7 mmol) of N-methyl-N-[3-phenyl-3-(2-pyridyl)propyl]-1,2-ethanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 1.15 g (5 mmol) of 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine as starting materials. Working up by chromatography (eluant: ethyl acetate/methanol 9+1) analogously to Example 63 yields the purified title compound in the form of a dry foam; MS (+FAB method): m/z (rel. int. [%])=527 ([M+H]+ 3), 196 (100).

Workup

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

Sources & evidence

ORD record
ord-f2d4129177b049bb8911f450de730329
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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