1,1'-Carbonyldiimidazole → HCID 178483447, compound

HRID 249015Notes

Reaction equation

HRID 249015 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].[NH:39]([C:43]1[S:44][CH:45]=[C:46]([CH2:48][S:49][CH2:50][CH2:51][NH2:52])[N:47]=1)[C:40]([NH2:42])=[NH:41]>>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:27]([NH:52][CH2:51][CH2:50][S:49][CH2:48][C:46]2[N:47]=[C:43]([NH:39][C:40]([NH2:42])=[NH:41])[S:44][CH:45]=2)=[O:28])[CH3:24])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762604HCID 19762604, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483447HCID 178483447, compound

Procedure

Preparation is effected analogously to Example 63, using 0.50 g (1.4 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine 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. [%])=616 ([M+H]+, 12), 229 (100); IR (KBr): 1640 cm-1 (C=O). For further analysis, a portion of the compound is converted into the tartaric acid salt in an ethanol/ether solvent mixture; m.p.: 95° C. (ethanol/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

Sources & evidence

ORD record
ord-4355d2a6c3b0423f93d864e29277bfe2
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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