1,1'-Carbonyldiimidazole → N-[2-[[5-[(dimethylamino)methyl]furfuryl]thio]ethyl]-N'-[3-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]propyl]urea

HRID 249020Notes

Reaction equation

HRID 249020 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][CH2:19][NH2:20])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25].[CH3:36][N:37]([CH2:39][C:40]1[O:49][C:43]([CH2:44][S:45][CH2:46][CH2:47][NH2:48])=[CH:42][CH:41]=1)[CH3:38]>>[CH3:38][N:37]([CH2:39][C:40]1[O:49][C:43]([CH2:44][S:45][CH2:46][CH2:47][NH:48][C:24]([NH:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]([CH2:6][C:5]2[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH3:21])=[O:25])=[CH:42][CH:41]=1)[CH3:36]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 19762569N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine

Product 1

HCID 19762606N-[2-[[5-[(dimethylamino)methyl]furfuryl]thio]ethyl]-N'-[3-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]propyl]urea

Procedure

Preparation is effected analogously to Example 63, using 0.57 g (1.8 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine 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. [%])=557 ([M+H]+, 1), 109 (100); IR (KBr): 1600 cm-1 (C=O). For further analysis, a portion of the compound is converted into the O,O'-ditoluoyltartaric acid salt in an ethanol/ether solvent mixture; m.p.: 102° C. (ethanol/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

Sources & evidence

ORD record
ord-1761a1a1e9a74ddcac455f31df20a96f
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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