Sodium Hydroxide → HCID 68595770, compound

HRID 220526Notes

Reaction equation

HRID 220526 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([C:22]4[CH:23]=[N:24][N:25]([CH:27]([CH3:29])[CH3:28])[CH:26]=4)=O)[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.CSC.B.[OH-].[Na+].[Cl-:36].[NH4+]>O1CCCC1.CO>[ClH:36].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([N:14]3[CH2:15][CH2:16][N:17]([CH2:20][C:22]4[CH:23]=[N:24][N:25]([CH:27]([CH3:29])[CH3:28])[CH:26]=4)[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 68596020HCID 68596020, compound

Product 1

HCID 68595770HCID 68595770, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve {4-[3-(4-fluoro-phenyl)-pyridin-2-yl]-piperazin-1-yl}-(1-isopropyl-1H-pyrazol-4-yl)-methanone (0.280 g, 0.712 mmol) in tetrahydrofuran (5 mL). Add borane dimethylsulfide (2 M in tetrahydrofuran, 0.64 mL, 1.28 mmol), and reflux the mixture for 18 hr. Cool the mixture to room temperature and carefully add a small amount of methanol then 2N sodium hydroxide (5 mL). Reflux the mixture for 2 hr. then cool and evaporate the organics. Add water and extract the mixture 3 times with ethyl acetate. Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 6:94 2 M ammonia in methanol:DCM), to give the free base white solid. Dissolve the free base in methanol and add ammonium chloride then sonicate the mixture for 10 min. Evaporate the solution to give the title compound as a white solid (0.127 g, 43%). MS (ES): m/z=380 [M+H]+.

Workup

  1. temperatureReflux the mixture for 2 hr
  2. temperaturethen cool
  3. customevaporate the organics
  4. extractionAdd water and extract the mixture 3 times with ethyl acetate
  5. dry with materialDry (sodium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 6:94 2 M ammonia in methanol:DCM)
  10. customto give the free base white solid
  11. customthen sonicate the mixture for 10 min
  12. customEvaporate the solution

Sources & evidence

ORD record
ord-2a341aa5083e4b1c8d992fe481a8a5e3
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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