1,1'-Carbonyldiimidazole → HCID 178483550, compound

HRID 249017Notes

Reaction equation

HRID 249017 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:8][CH2:9][CH2:10][N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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]>>[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:8][CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:24]([NH:49][CH2:48][CH2:47][S:46][CH2:45][C:43]2[N:44]=[C:40]([NH:36][C:37]([NH2:39])=[NH:38])[S:41][CH:42]=2)=[O:25])[CH3:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762562HCID 19762562, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483550HCID 178483550, compound

Procedure

Preparation is effected analogously to Example 63, using 0.37 g (1.2 mmol) of N-[2-(diphenylmethoxy)ethyl]-N-methyl-1,4-butanediamine 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. [%])=570 ([M+H]+, 11), 167 (100); IR (KBr): 1644 cm-1 (C=O). For further analysis, a portion of the compound is converted into the tartaric acid salt and recrystallised from acetonitrile/isopropanol/petroleum ether; m.p.: 101° C. (acetonitrile/isopropanol/petroleum 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
  4. customrecrystallised from acetonitrile/isopropanol/petroleum ether

Sources & evidence

ORD record
ord-e4995dae8ed148708386c9cdaecc9944
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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