N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea → N-cyano-N'-[4-[N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]-butyl]-N"-[3-[3-(piperidinomethyl)phenoxy]propyl]guanidine
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]([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:24]([NH:26][C:27]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:17])=[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[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]2)[CH:41]=1)#[N:25]Participants
3
Procedure
Preparation is effected analogously to Example 1, using 0.8 g (2.5 mmol) of N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,4-butanediamine and 0.99 g (2.5 mmol) of N-cyano-O-phenyl-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]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.[%])=614 ([M+H]+, 3), 214 (50.2), 154 ([m-NO2 -benzylOH], 100); IR (KBr): 2163 cm-1 (C≡N). For analytical purposes a sample is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from ether/isopropanol; m.p.: 105°-110° C. with decomposition.
Workup
- customPreparation
- customWorking up by chromatography analogously to Example 1 yields the
- custompurified title compound in the form of a viscous oil
- customrecrystallised from ether/isopropanol
Sources & evidence
- ORD record
- ord-83ecae2375ef4608b059f0370f83612b
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212187
Reaction notes
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