1,1'-Carbonyldiimidazole → N-[2-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]ethyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

HRID 248990Notes

Reaction equation

HRID 248990 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].[N:35]1([CH2:41][C:42]2[CH:43]=[C:44]([CH:50]=[CH:51][CH:52]=2)[O:45][CH2:46][CH2:47][CH2:48][NH2:49])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH2:17][CH2:18][NH:19][C:23]([NH:49][CH2:48][CH2:47][CH2:46][O:45][C:44]2[CH:50]=[CH:51][CH:52]=[C:42]([CH2:41][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:43]=2)=[O:24])[CH3:20])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 19762513HCID 19762513, compound

Product 1

HCID 19762588N-[2-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]ethyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

Procedure

Preparation is effected analogously to Example 63, using 0.42 g (1.0 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,2-ethanediamine and the equimolar amounts of 1,1'-carbonyldiimidazole and 3-[3-(piperidinomethyl)phenoxy]propylamine as starting materials. Working up by chromatography analogously to Example 63 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=577 ([M+H]+, 12), 229 (99), 109 (100); IR (KBr): 1640 cm-1 (C=O). For further analysis, a portion of the compound is converted into the tartaric acid salt and recrystallised from isopropanol/ether/petroleum ether; m.p.: 68° C. (isopropanol/ether/petroleum ether).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 63 yields the
  3. custompurified title compound in the form of a viscous oil
  4. customrecrystallised from isopropanol/ether/petroleum ether

Sources & evidence

ORD record
ord-5c80cd5a682146f0b19d8dcc970cf93a
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

Loading…