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

HRID 248986Notes

Reaction equation

HRID 248986 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][CH2:19][NH2:20])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:24]([NH:26][C:27](=[N:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][N:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)[CH:42]=1)OC1C=CC=CC=1)#[N:25]>>[C:24]([NH:26][C:27]([NH:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]([CH2:6][C:5]1[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:21])=[N:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][N:48]2[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]2)[CH:42]=1)#[N:25]

Participants

3

Reactant 2

HCID 14026191N-cyano-O-phenyl-N'-[4-[3-(piperidinomethyl)phenoxy]butyl]isoureaHCID 19762569N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine

Product 1

HCID 178483801N-cyano-N'-[3-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]propyl]-N"-[4-[3-(piperidinomethyl)phenoxy]butyl]guanidine

Procedure

Preparation is effected analogously to Example 1, using 0.50 g (1.6 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine and the equimolar amount of N-cyano-O-phenyl-N'-[4-[3-(piperidinomethyl)phenoxy]butyl]isourea as starting materials. Working up by chromatography analogously to Example 1 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=629 ([M+H]+, 18), 229 (98), 109 (100); IR (KBr): 2164 cm-1 (C≡N). For further analysis, a portion of the compound is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from isopropanol/ether; m.p.: 102°-105° C. (isopropanol/ether).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 1 yields the
  3. custompurified title compound in the form of a viscous oil
  4. customrecrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-1f48833afe1e433da437afd046e71bb6
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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