Water → HCID 117988185, compound

HRID 2206122Notes

Reaction equation

HRID 2206122 reaction equation
[CH:1]1([C:6]2[C:14]3[C:9](=[C:10]([O:15]C)[N:11]=[CH:12][CH:13]=3)[N:8]([C:17]3[CH:18]=[C:19]([C:22]([NH2:24])=[O:23])[S:20][CH:21]=3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C>[CH:1]1([C:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[N:8]([C:17]3[CH:18]=[C:19]([C:22]([NH2:24])=[O:23])[S:20][CH:21]=3)[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 117987901HCID 117987901, compound

Product 1

HCID 117988185HCID 117988185, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(3-cyclopentyl-7-methoxy-1H-pyrazolo[3,4-c]pyridin-1-yl)thiophene-2-carboxamide (60 mg) in acetonitrile (5 mL) were added sodium iodide (52.5 mg) and chloro(trimethyl)silane (0.111 mL), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by HPLC (L-Column 2 ODS, mobile phase: water/acetonitrile (containing 0.1% trifluoroacetic acid)), to the obtained fraction was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate and THF. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The suspension of the residue in ethanol was stirred at 100° C. for 2 hr, allowed to be cooled to room temperature, and the solid was washed with ethanol to give the title compound (35 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by HPLC (L-Column 2 ODS, mobile phase: water/acetonitrile (containing 0.1% trifluoroacetic acid)), to the obtained fraction
  6. additionwas added saturated aqueous sodium hydrogencarbonate solution
  7. extractionthe mixture was extracted with ethyl acetate and THF
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionThe suspension of the residue in ethanol
  11. stirringwas stirred at 100° C. for 2 hr
  12. temperatureto be cooled to room temperature
  13. washthe solid was washed with ethanol

Sources & evidence

ORD record
ord-42e04a0c6c5e4383af960979775b94e5
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…