Hydrochloric Acid → HCID 178423771, compound

HRID 1188099Notes

Reaction equation

HRID 1188099 reaction equation
O1CCCCC1[N:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:10][C:9]([C:19]([NH:21][C:22]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[N:24](C3CCCCO3)[N:23]=2)=O)=[N:8]1.CO.Cl>C1COCC1>[C:30]1([CH3:33])[CH:31]=[CH:32][C:27]([C:25]2[NH:24][N:23]=[C:22]([NH:21][CH2:19][C:9]3[CH:10]=[C:11]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=4)[NH:7][N:8]=3)[CH:26]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59408738HCID 59408738, compound

Product 1

HCID 178423771HCID 178423771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(Tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-yl)-5-p-tolyl-1H-pyrazole-3-carboxamide (142 mg, 0.27 mmol) was suspended in anhydrous THF (10 mL) and borane dimethylsulfide complex (177 μL, 1.86 mmol) was added dropwise. The reaction mixture was stirred under reflux for 16 hrs. The reaction mixture was then cooled down to 0° C. and MeOH (500 μL) was added. The mixture was then stirred for 10 min. Concentrated hydrochloric acid (12 N) was added, until a pH<2 was obtained, and the resulting mixture was stirred under reflux for 16 hrs. The mixture was cooled to room temperature and the precipitate was filtered and added into an aqueous solution of sodium hydroxide (1M). The aqueous phase was extracted with DCM (3×10 mL) after drying the organic layers with Na2SO4, the solvent was evaporated. The residue was purified by chromatography on silica gel column (eluent: EtOAc); 5-p-tolyl-N-((5-p-tolyl-1H-pyrazol-3-yl)methyl)-1H-pyrazol-3-amine was obtained as a white solid.

Workup

  1. additionborane dimethylsulfide complex (177 μL, 1.86 mmol) was added dropwise
  2. temperatureunder reflux for 16 hrs
  3. stirringThe mixture was then stirred for 10 min
  4. customwas obtained
  5. stirringthe resulting mixture was stirred
  6. temperatureunder reflux for 16 hrs
  7. temperatureThe mixture was cooled to room temperature
  8. filtrationthe precipitate was filtered
  9. additionadded into an aqueous solution of sodium hydroxide (1M)
  10. extractionThe aqueous phase was extracted with DCM (3×10 mL)
  11. dry with materialafter drying the organic layers with Na2SO4
  12. customthe solvent was evaporated
  13. customThe residue was purified by chromatography on silica gel column (eluent: EtOAc)

Sources & evidence

ORD record
ord-751be4e8506b4776aba1e98b88ad1cfb
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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