1,1'-Carbonyldiimidazole → N-[2-[[5-[(dimethylamino)methyl]furfuryl]thio]ethyl]-N'-[2-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]ethyl]urea

HRID 249019Notes

Reaction equation

HRID 249019 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].[CH3:35][N:36]([CH2:38][C:39]1[O:48][C:42]([CH2:43][S:44][CH2:45][CH2:46][NH2:47])=[CH:41][CH:40]=1)[CH3:37]>>[CH3:37][N:36]([CH2:38][C:39]1[O:48][C:42]([CH2:43][S:44][CH2:45][CH2:46][NH:47][C:23]([NH:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]([CH2:6][C:5]2[CH:21]=[CH:22][C:2]([F:1])=[CH:3][CH:4]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH3:20])=[O:24])=[CH:41][CH:40]=1)[CH3:35]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 19762513HCID 19762513, compound

Product 1

HCID 19762603N-[2-[[5-[(dimethylamino)methyl]furfuryl]thio]ethyl]-N'-[2-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]ethyl]urea

Procedure

Preparation is effected analogously to Example 63, using 0.56 g (1.8 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,2-ethanediamine and the equimolar amounts of 1,1'-carbonyldiimidazole and 2-[[5-[(dimethylamino)methyl]-furfuryl]thio]ethylamine as starting materials. Working up by chromatography analogously to Example 1 yields the purified title compound in the form of a viscous oil; MS(+FAB method): m/z (rel. int. [%])=543 ([M+H]+, 14), 109 (100); IR (KBr): 1641 cm-1 (C=O). For further analysis, a portion of the compound is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from isopropanol/ether; m.p.: 90° C. (isopropanol/ether).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 1 yields the
  3. custompurified title compound in the form of a viscous oil
  4. customrecrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-8ed1b42f2ebe464082f2704c3d8f32e7
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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