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Water → 1-{5-[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one

HRID 2411723
Notes
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Reaction equation

HRID 2411723 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH:9]1([C:12]2[CH:13]=[C:14]([CH3:34])[C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4[CH:27]=[N:28][C:29](F)=[CH:30][C:31]=4[CH3:32])=[O:25])[CH2:20][CH2:19]3)=[N:16][CH:17]=2)[CH2:11][CH2:10]1.O>CN(C)C=O>[CH:9]1([C:12]2[CH:13]=[C:14]([CH3:34])[C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4[C:31]([CH3:32])=[CH:30][C:29]([N:3]5[CH2:7][CH2:6][CH2:5][C:4]5=[O:8])=[N:28][CH:27]=4)=[O:25])[CH2:20][CH2:19]3)=[N:16][CH:17]=2)[CH2:10][CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 58484562HCID 58484562, compound

Product 1

HCID 712519061-{5-[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

Under a nitrogen stream, sodium hydride (47 mg) was suspended in N,N-dimethylformamide (10 mL), pyrrolidin-2-one (74 μL) was added, and the mixture was stirred at room temperature. Then, a solution of [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (210 mg) described in Preparation Example 140 in N,N-dimethylformamide (5 mL) was added, and the mixture was stirred at 95° C. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography to give 1-{5-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one. The obtained 1-{5-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one was dissolved in dichloromethane, 1N hydrogen chloride/diethyl ether (5 mL) was added, and the precipitate was collected by filtration to give the title compound (12 mg).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 95° C
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-aabd3470558b42c594246f2b683d988d
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08816079B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes