1,1'-Carbonyldiimidazole → HCID 178483431, compound

HRID 248963Notes

Reaction equation

HRID 248963 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:9][CH2:10][N:11]([CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])=[CH:4][CH:3]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29].[NH:40]([C:44]1[S:45][CH:46]=[C:47]([CH2:49][S:50][CH2:51][CH2:52][NH2:53])[N:48]=1)[C:41]([NH2:43])=[NH:42]>C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:28]([NH:53][CH2:52][CH2:51][S:50][CH2:49][C:47]2[N:48]=[C:44]([NH:40][C:41]([NH2:43])=[NH:42])[S:45][CH:46]=2)=[O:29])[CH3:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762614HCID 19762614, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483431HCID 178483431, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.6 g (1.6 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,8-octanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.4 g (1.7 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, DMSO/MNBA): m/z (rel. int.[%])=645 ([M+H]+,<1), 234 (100); IR (KBr): 1638 cm-1 (C=O). For analytical purposes a sample is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from ether/isopropanol; m.p.: 135°-140° C.

Workup

  1. customPreparation
  2. custompurified title compound in the form of a dry foam
  3. customrecrystallised from ether/isopropanol

Sources & evidence

ORD record
ord-680fe515cbec47c9bacba6d1751e1f78
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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