N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea → N-[4-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]butyl]-N'-cyano-N"-[3-[3-(piperidinomethyl)phenoxy]propyl]guanidine

HRID 248934Notes

Reaction equation

HRID 248934 reaction equation
[Cl: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]([NH:26][C:27](=[N:35][CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH:41]=1)OC1C=CC=CC=1)#[N:25]>C(Cl)Cl.CO>[Cl: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:27]([NH:26][C:24]#[N:25])=[N:35][CH2:36][CH2:37][CH2:38][O:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)[CH:41]=2)[CH3:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13486636N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isoureaHCID 19762494N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,4-butanediamine

Product 1

HCID 54019736N-[4-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]butyl]-N'-cyano-N"-[3-[3-(piperidinomethyl)phenoxy]propyl]guanidine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Preparation is effected analogously to Example 1, using 0.99 g (3 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,4-butanediamine and 1.17 g (3 mmol) of N-cyano-O-phenyl-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]isourea as starting materials. Working up by chromatography (eluant: methylene chloride/methanol 98+2) analogously to Example 1 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int.[%])=630 ([M+H]+, 7), 230 (100); IR (KBr): 2164 cm-1 (C≡N).

Workup

  1. customPreparation
  2. custompurified title compound in the form of a viscous oil

Sources & evidence

ORD record
ord-1fa1fdc3770148c09795aa988594020b
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

Loading…