N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea → N-cyano-N'-[5-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]pentyl]-N"-[3-[3-(piperidinomethyl)phenoxy]propyl]guanidine
Reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:26]([NH:28][C:29](=[N:37][CH2:38][CH2:39][CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][N:49]2[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]2)[CH:43]=1)OC1C=CC=CC=1)#[N:27]>>[C:26]([NH:28][C:29]([NH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]([CH2:6][C:5]1[CH:24]=[CH:25][C:2]([F:1])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:23])=[N:37][CH2:38][CH2:39][CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][N:49]2[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]2)[CH:43]=1)#[N:27]Participants
3
Procedure
Preparation is effected analogously to Example 1, using 0.54 g (1.6 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,5-pentanediamine and the equimolar amount 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. %]) =643 ([M+H]+, 7), 229 (54), 154 ([m-NO2 -benzylOH] 100); IR (KBr): 2165 cm-1 (C≡N). For further analysis, a portion of the compound is converted into the tartaric acid salt which forms a dry foam under reduced pressure.
Workup
- customPreparation
- customWorking up by chromatography analogously to Example 1 yields the
- custompurified title compound in the form of a viscous oil
Sources & evidence
- ORD record
- ord-92370dfaba994538ac9625567f6656d1
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212187
Reaction notes
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