1,1'-Carbonyldiimidazole → HCID 178491106, compound

HRID 249009Notes

Reaction equation

HRID 249009 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:22])[CH2:18][CH2:19][CH2:20][NH2:21])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[C:25](N1C=CN=C1)(N1C=CN=C1)=[O:26].[NH:37]([C:41]1[S:42][CH:43]=[C:44]([CH2:46][S:47][CH2:48][CH2:49][NH2:50])[N:45]=1)[C:38]([NH2:40])=[NH:39]>>[NH:37]([C:41]1[S:42][CH:43]=[C:44]([CH2:46][S:47][CH2:48][CH2:49][NH:50][C:25]([NH:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:8]([CH2:7][C:6]2[CH:23]=[CH:24][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH3:22])=[O:26])[N:45]=1)[C:38]([NH2:40])=[NH:39]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762492HCID 19762492, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178491106HCID 178491106, compound

Procedure

Preparation is effected analogously to Example 63, using 1.00 g (3.0 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine and the equimolar amounts of 1,1'-carbonyldiimidazole and 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine as starting materials. Working up by chromatography analogously to Example 63 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=586 ([M+H]+, 4), 121 (100); IR (KBr): 1717 cm-1 (C=O). For further analysis, a portion of the compound is converted into the picric acid salt and recrystallised from ethanol; m.p.: 106°-109° C. (ethanol).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 63 yields the
  3. custompurified title compound in the form of a viscous oil
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-af44303a8e874b05a2252ab6e47e34d3
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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