1,1'-Carbonyldiimidazole → HCID 178484354, compound

HRID 248968Notes

Reaction equation

HRID 248968 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:9][CH2:10][N:11]([CH3:15])[CH2:12][CH2:13][NH2:14])=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[NH:34]([C:38]1[S:39][CH:40]=[C:41]([CH2:43][S:44][CH2:45][CH2:46][NH2:47])[N:42]=1)[C:35]([NH2:37])=[NH:36]>C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][NH:14][C:22]([NH:47][CH2:46][CH2:45][S:44][CH2:43][C:41]2[N:42]=[C:38]([NH:34][C:35]([NH2:37])=[NH:36])[S:39][CH:40]=2)=[O:23])[CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762518N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamineHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178484354HCID 178484354, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.9 g (2.9 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamine, 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: methylene chloride/methanol 95+5) analogously to Example 63 yields the purified title compound in the form of an oil; MS (+FAB method): m/z (rel. int.[%])=561 ([M+H]+, 3), 155 (26), 230 (100); IR (KBr): 1650 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.: from 140° C. with decomposition.

Workup

  1. customPreparation
  2. custompurified title compound in the form of an oil
  3. customrecrystallised from ether/isopropanol
  4. customfrom 140° C.

Sources & evidence

ORD record
ord-cc7722aec3cc45c2aafa4daa87172b3e
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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