1,1'-Carbonyldiimidazole → N-[3-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]propyl]-N'-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]urea

HRID 248976Notes

Reaction equation

HRID 248976 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].[CH3:35][C:36]1[NH:40][CH:39]=[N:38][C:37]=1[CH2:41][S:42][CH2:43][CH2:44][NH2:45]>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:45][CH2:44][CH2:43][S:42][CH2:41][C:37]2[N:38]=[CH:39][NH:40][C:36]=2[CH3:35])=[O:24])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 19762536HCID 19762536, compound

Product 1

HCID 19762555N-[3-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]propyl]-N'-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]urea

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.8 g (2.5 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,3-propanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.5 g (2.9 mmol) of 2-[[(5-methylimidazol-4-yl)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 crystalline solid; m.p.(ether): 102°-104° C.; MS (+FAB method): m/z (rel. int.[%])=515 ([M+H]+, 10), 95 (75), 230 (100).

Workup

  1. customPreparation
  2. custompurified title compound in the form of a crystalline solid
  3. custom102°-104° C.

Sources & evidence

ORD record
ord-d657ad86179e43ed94c7cbb76356b6a9
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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