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

HRID 248975Notes

Reaction equation

HRID 248975 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:9][CH2:10][N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:4][CH:3]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25].[CH3:36][C:37]1[NH:41][CH:40]=[N:39][C:38]=1[CH2:42][S:43][CH2:44][CH2:45][NH2:46]>C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:24]([NH:46][CH2:45][CH2:44][S:43][CH2:42][C:38]2[N:39]=[CH:40][NH:41][C:37]=2[CH3:36])=[O:25])[CH3:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 19762494N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,4-butanediamine

Product 1

HCID 19762554N-[4-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]butyl]-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 (2.4 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,4-butanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.5 g (2.9 mmol) of 2-[[(5-methylimidazol-4-yl)methyl]thio]ethaneamine [R. W. Brimblecombe et al., J. Int. Med. Res. 3, 86 (1975)] 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 that is recrystallised from ether; m.p.: 97°-98° C.; MS (+FAB method): m/z (rel. int.[%])=529 ([M+H]+, 10), 230 (100); IR (KBr): 1643 cm-1 (C=O).

Workup

  1. customPreparation
  2. custompurified title compound in the form of a crystalline solid
  3. customthat is recrystallised from ether

Sources & evidence

ORD record
ord-2b3b8c3cc6314e3488b7e60f2db65cee
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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