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Water → Piperazine,1-[6-[3-(3-methylbutyl)-2-oxo-1-imidazolidinyl]-3-pyridazinyl]-4-[2-(trifluoromethyl)benzoyl]-

HRID 499164
Notes
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Reaction equation

HRID 499164 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[N:17][C:16]([N:19]3[CH2:23][CH2:22][NH:21][C:20]3=[O:24])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6].[H-].[Na+].I[CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37].O>CN(C=O)C>[CH3:37][CH:36]([CH3:38])[CH2:35][CH2:34][N:21]1[CH2:22][CH2:23][N:19]([C:16]2[N:17]=[N:18][C:13]([N:10]3[CH2:9][CH2:8][N:7]([C:5](=[O:6])[C:4]4[CH:25]=[CH:26][CH:27]=[CH:28][C:3]=4[C:2]([F:1])([F:29])[F:30])[CH2:12][CH2:11]3)=[CH:14][CH:15]=2)[C:20]1=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 109241-Iodo-3-methylbutaneHCID 24758Sodium hydrideHCID 115608011-{6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazin-3-yl}imidazolidin-2-one

Product 1

HCID 11684584Piperazine,1-[6-[3-(3-methylbutyl)-2-oxo-1-imidazolidinyl]-3-pyridazinyl]-4-[2-(trifluoromethyl)benzoyl]-Yield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazin-3-yl}imidazolidin-2-one (0.080 g, 0.180 mmol), sodium hydride in 60% mineral oil (0.0035 g, 0.150 mmol) in DMF (10 mL) was stirred at room temperature for 30 minutes. 1-Iodo-3-methylbutane (0.0376 g, 0.190 mmol) was added and the mixture was stirred at 60° C. for 24 hours, followed by the dilution with 50 mL of water, and then extracted with ethyl acetate (100 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The title compound was obtained as a pale yellow solid in 32% yield (0.028 mg) after column chromatography purification. 1H NMR (300 MHz, CDCl3) δ 8.45 (d, J=9.9 Hz, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.48-7.65 (m, 2H), 7.32 (d, J=7.5 Hz, 1H), 6.98 (d, J=9.9 Hz, 1H), 3.82-4.12 (m, 4H), 3.42-3.64 (m, 6H), 3.24-3.34 (m, 4H), 1.38-1.66 (m, 3H), 0.92 (d, J=6.5 Hz, 6H). 13C NMR (75 MHz, CDCl3) δ 167.8, 157.3, 150.5, 134.8, 132.6, 129.7, 127.5, 127.1, 125.8, 122.1, 120.4, 116.6, 46.8, 46.3, 45.9, 42.5, 42.1, 41.5, 36.5, 26.1, 22.8. MS (ES+) m/z 491 (M+1).

Workup

  1. stirringthe mixture was stirred at 60° C. for 24 hours
  2. extractionextracted with ethyl acetate (100 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b0f8ee6f211f4f869f875c737bfae675
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767677B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes