1,1'-Carbonyldiimidazole → N-[5-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]-pentyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

HRID 248993Notes

Reaction equation

HRID 248993 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](N1C=CN=C1)(N1C=CN=C1)=[O:27].[N:38]1([CH2:44][C:45]2[CH:46]=[C:47]([CH:53]=[CH:54][CH:55]=2)[O:48][CH2:49][CH2:50][CH2:51][NH2:52])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:26]([NH:52][CH2:51][CH2:50][CH2:49][O:48][C:47]2[CH:53]=[CH:54][CH:55]=[C:45]([CH2:44][N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH:46]=2)=[O:27])[CH3:23])[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 19762527HCID 19762527, compound

Product 1

HCID 19762607N-[5-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]-pentyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

Procedure

Preparation is effected analogously to Example 63, using 0.51 g (1.5 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,5-pentanediamine 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. [%])=619 ([M+H]+, 3), 77 (100); IR (KBr): 1634 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.: 63° 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-178c147c04b441c6b287dc0b404a6550
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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