1,1'-Carbonyldiimidazole → HCID 178483546, compound

HRID 248972Notes

Reaction equation

HRID 248972 reaction equation
[CH3:1][N:2]([CH2:8][CH2:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[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]>C(OCC)(=O)C.CO>[NH:35]([C:39]1[S:40][CH:41]=[C:42]([CH2:44][S:45][CH2:46][CH2:47][NH:48][C:23]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH2:8][CH2:9][CH:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH3:1])=[O:24])[N:43]=1)[C:36]([NH2:38])=[NH:37]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762597N-methyl-N-[3-phenyl-3-(2-pyridyl)propyl]-1,4-butanediamineHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483546HCID 178483546, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.89 g (3 mmol) of N-methyl-N-[3-phenyl-3-(2-pyridyl)propyl]-1,4-butanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.75 g (3.2 mmol) of 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine as starting materials. Working up by chromatography (eluant: chloroform/methanol 9+1) analogously to Example 63 yields the purified title compound in the form of a dry foam; MS (+FAB method): m/z (rel. int.[%])=555 ([M+H]+ 1), 196 (100); IR (KBr): 1610 cm-1 (C=O). For analytical purposes a sample is converted into the maleic acid salt and recrystallised from ether/ethanol; m.p.: from 80° C. with decomposition.

Workup

  1. customPreparation
  2. custompurified title compound in the form of a dry foam
  3. customrecrystallised from ether/ethanol
  4. customfrom 80° C.

Sources & evidence

ORD record
ord-88d71ecffe7f48278000d7dd4b22c3ee
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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