1,1'-Carbonyldiimidazole → N-[4-[N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]butyl]-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]urea

HRID 248970Notes

Reaction equation

HRID 248970 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:9][CH2:10][N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:4][CH:3]=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(OCC)(=O)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[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:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19762522HCID 19762522, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178483548N-[4-[N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]butyl]-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]urea

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.95 g (3.5 mmol) of N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,4-butanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.82 g (3.5 mmol) of 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine as starting materials. Working up by chromatography (eluant: ethyl acetate/methanol 9+1) analogously to Example 63 yields the purified title compound in the form of a dry foam; MS (+FAB method): m/z (rel. int.[%])=573 ([M+H]+ 2), 214 (100); IR (KBr): 1632 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 120° C. with decomposition.

Workup

  1. customPreparation
  2. custompurified title compound in the form of a dry foam
  3. customrecrystallised from ether/isopropanol
  4. customfrom 120° C.

Sources & evidence

ORD record
ord-35146e8d9526490d80d0db2ba3238578
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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