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

HRID 248977Notes

Reaction equation

HRID 248977 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:9][CH2:10][N:11]([CH3:15])[CH2:12][CH2:13][NH2:14])=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[CH3:34][C:35]1[NH:39][CH:38]=[N:37][C:36]=1[CH2:40][S:41][CH2:42][CH2:43][NH2:44]>C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][NH:14][C:22]([NH:44][CH2:43][CH2:42][S:41][CH2:40][C:36]2[N:37]=[CH:38][NH:39][C:35]=2[CH3:34])=[O:23])[CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 19762518N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamine

Product 1

HCID 19762510N-[2-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]ethyl]-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 (2.6 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.5 g (2.8 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): 114° C.; MS (+FAB method): m/z (rel. int.[%])=501 ([M+H]+, 15), 95 (63), 230 (100); IR (KBr): 1640 cm-1 (C=O).

Workup

  1. customPreparation
  2. custompurified title compound in the form of a crystalline solid
  3. custom114° C.

Sources & evidence

ORD record
ord-b4ece43fabc74262979a250d8ed846e9
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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