N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea → HCID 54452316, compound

HRID 248982Notes

Reaction equation

HRID 248982 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:22])[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:25]([NH:27][C:28](=[N: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:26]>>[C:25]([NH:27][C:28]([NH:21][CH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]([CH2:6][C:5]1[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:22])=[N: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:26]

Participants

3

Reactant 2

HCID 13486636N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isoureaHCID 19762574N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,4-butanediamine

Product 1

HCID 54452316HCID 54452316, compound

Procedure

Preparation is effected analogously to Example 1, using 0.33 g (1.0 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,4-butanediamine 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. [%])=629 ([M+H]+, 5), 229 (84), 109 (100); IR (KBr): 2166 cm-1 (C≡N). For further analysis, a portion of the compound is converted into the tartaric acid salt and recrystallised from ethanol/acetonitrile/isopropanol; m.p. 84°-86° C. (ethanol/acetonitrile/isopropanol).

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 ethanol/acetonitrile/isopropanol

Sources & evidence

ORD record
ord-ccbb71e802d045de8e4d3a16077a682e
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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