1,1'-Carbonyldiimidazole → HCID 178491108, compound

HRID 249008Notes

Reaction equation

HRID 249008 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:21])[CH2:18][CH2:19][NH2:20])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25].[NH:36]([C:40]1[S:41][CH:42]=[C:43]([CH2:45][S:46][CH2:47][CH2:48][NH2:49])[N:44]=1)[C:37]([NH2:39])=[NH:38]>>[NH:36]([C:40]1[S:41][CH:42]=[C:43]([CH2:45][S:46][CH2:47][CH2:48][NH:49][C:24]([NH:20][CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH3:21])=[O:25])[N:44]=1)[C:37]([NH2:39])=[NH:38]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762590N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,2-ethanediamineHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178491108HCID 178491108, compound

Procedure

Preparation is effected analogously to Example 63, using 0.53 g (1.7 mmol) of N-[2-[N-(4-methoxybenzyl)-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. [%])=572 ([M+H]+, 1), 121 (100); IR (KBr): 1644 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.: 84° 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-48466b1f9b154f4f89699a9a66a1f7aa
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

Loading…