1,1'-Carbonyldiimidazole → HCID 178484355, compound

HRID 249012Notes

Reaction equation

HRID 249012 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].[NH:35]([C:39]1[S:40][CH:41]=[C:42]([CH2:44][S:45][CH2:46][CH2:47][NH2:48])[N:43]=1)[C:36]([NH2:38])=[NH:37]>>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH2:17][CH2:18][NH:19][C:23]([NH:48][CH2:47][CH2:46][S:45][CH2:44][C:42]2[N:43]=[C:39]([NH:35][C:36]([NH2:38])=[NH:37])[S:40][CH:41]=2)=[O:24])[CH3:20])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762513HCID 19762513, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178484355HCID 178484355, compound

Procedure

Preparation is effected analogously to Example 63, using 0.29 g (0.97 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-[[(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. [%])=560 ([M+H]+, 8), 78 (100); IR (KBr): 1659 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.: 132° C. (ethanol/ether).

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

Sources & evidence

ORD record
ord-472e889e469448ad9a0a2fc15dea3571
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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