1,1'-Carbonyldiimidazole → HCID 178491104, compound

HRID 249010Notes

Reaction equation

HRID 249010 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27].[NH:38]([C:42]1[S:43][CH:44]=[C:45]([CH2:47][S:48][CH2:49][CH2:50][NH2:51])[N:46]=1)[C:39]([NH2:41])=[NH:40]>>[NH:38]([C:42]1[S:43][CH:44]=[C:45]([CH2:47][S:48][CH2:49][CH2:50][NH:51][C:26]([NH:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:8]([CH2:7][C:6]2[CH:24]=[CH:25][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH3:23])=[O:27])[N:46]=1)[C:39]([NH2:41])=[NH:40]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762580HCID 19762580, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178491104HCID 178491104, compound

Procedure

Preparation is effected analogously to Example 63, using 0.54 g (1.58 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]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. [%])=600 ([M+H]+, 1), 121 (100); IR (KBr): 1599 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.: 104°-106° 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-73f38495c24247c2ad53c1ac5cd248be
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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