Potassium Hydroxide → 1-{6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazin-3-yl}imidazolidin-2-one

HRID 499163Notes

Reaction equation

HRID 499163 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:6].[OH-].[K+]>C(O)CCC>[F:28][C:27]([F:30])([F:29])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[N:10]=[N:9][C:8]([N:7]3[CH2:2][CH2:3][NH:4][C:5]3=[O:6])=[CH:13][CH:12]=2)[CH2:15][CH2:16]1)=[O:31]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 113400561-(2-Chloroethyl)-3-{6-[4-(2-trifluoromethylbenzoyl)-piperazin-1-YL]pyridazin-3-YL}urea

Product 1

HCID 115608011-{6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazin-3-yl}imidazolidin-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1-(2-chloroethyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridazin-3-yl}urea (0.296 g, 0.650 mmol), potassium hydroxide (0.364 g, 0.650 mmol), in BuOH (20 mL) was refluxed overnight. The reaction mixture was concentrated and purified by column chromatography. The title compound was obtained as a light yellow powder in 71% yield (0.213 g). 1H NMR (300 MHz, CDCl3) δ 8.43 (d, J=9.9 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.48-1.64 (m, 2H), 7.34 (d, J=7.5 Hz, 1H), 7.01 (d, J=9.9 Hz, 1H), 4.91-5.12 (br., 1H), 4.22 (t, J=7.8 Hz, 1H), 3.82-4.03 (m, 2H), 3.43-3.65 (m, 6H), 3.31 (t, J=5.7 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-eca148f308c844cc9a89b6aefba12864
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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