1,1'-Carbonyldiimidazole → HCID 178483437, compound

HRID 249016Notes

Reaction equation

HRID 249016 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[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]>>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][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])[CH3:25])[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 19762519HCID 19762519, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483437HCID 178483437, compound

Procedure

Preparation is effected analogously to Example 63, using 0.59 g (1.6 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,7-heptanediamine 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. [%])=630 ([M+H]+, 3), 109 (100); IR (KBr): 1666 cm-1 (C=O). For further analysis, a portion of the compound is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from isopropanol/ether; m.p.: 125° C. (isopropanol/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 isopropanol/ether

Sources & evidence

ORD record
ord-05cd5d3dfa854029ab62a1e86165c1e6
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

Loading…