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Water → 1-[3-(2,4,5-Trifluorophenyl)propyl]-3-(4-tert-butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone

HRID 1295702
Notes
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Reaction equation

HRID 1295702 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15](=[O:20])[NH:16][CH:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].CS(O[CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[CH:37][C:36]=1[F:43])(=O)=O.O>C1COCC1.CCOC(C)=O>[F:43][C:36]1[CH:37]=[C:38]([F:42])[C:39]([F:41])=[CH:40][C:35]=1[CH2:34][CH2:33][CH2:32][N:16]1[CH:17]=[CH:18][N:19]=[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)[C:15]1=[O:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 590138923-(4-tert-Butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinoneHCID 86591618HCID 86591618, compound

Product 1

HCID 693661361-[3-(2,4,5-Trifluorophenyl)propyl]-3-(4-tert-butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinoneYield 86.8%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-tert-butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone (obtained in Example 48, Step 1; 0.53 g, 1.91 mmol) in THF (10 mL) was added t-BuOK (0.21 g, 1.91 mmol) and the mixture was stirred at room temperature for 10 min. The resultant mixture was added dropwise to a solution of 3-(2,4,5-trifluorophenyl)propyl methanesulfonate (0.66 g, ˜2.1 mmol; from Step 3) in THF (10 mL). The mixture was stirred at 35° C. for 3 days. Then, the solution was cooled to 0° C. and water (20 mL) and EtOAc (25 mL) were added. The aqueous phase was saturated with NaCl (2 g) and extraction performed. After separation and repeated extraction with EtOAc (15 mL) the combined organic layers were washed with brine and dried over Na2SO4. Concentration in vacuum gave 0.75 g of a yellowish oil which was purified by column chromatography on silica gel using EtOAc/n-hexane (4:1) as eluent. This gave 0.50 g (57%) of the title compound as a colorless oil. HPLC purity: 91%. 1H NMR and MS analyses support the stated structure.

Workup

  1. stirringThe mixture was stirred at 35° C. for 3 days
  2. temperatureThen, the solution was cooled to 0° C.
  3. extractionThe aqueous phase was saturated with NaCl (2 g) and extraction
  4. customAfter separation
  5. extractionextraction with EtOAc (15 mL) the combined organic layers
  6. washwere washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationConcentration in vacuum

Sources & evidence

ORD record
ord-4b1b10c182c2489f9e370aefe609275d
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07244722B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes