Sodium Iodide → HCID 136950916, compound

HRID 2206227Notes

Reaction equation

HRID 2206227 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][N:11]=[C:10]([O:15]C)[C:9]=3[C:8]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[C:8]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:25])=[O:26])=[CH:20][CH:19]=3)=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 117987732HCID 117987732, compound

Product 1

HCID 136950916HCID 136950916, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate (150 mg) obtained in Step C of Example 12 in toluene (20 ml) were added 4-aminobenzenesulfonamide (212 mg), tris(dibenzylideneacetone)dipalladium (37.6 mg), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)(47.5 mg) and cesium carbonate (669 mg), and the mixture was heated overnight with reflux under nitrogen atmosphere. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was washed successively with hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue (105 mg) containing 4-((1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)amino)benzenesulfonamide. To a solution of the obtained residue (102 mg) in acetonitrile (10 mL) were added sodium iodide (64.8 mg) and chloro(trimethyl)silane (0.219 mL), and the mixture was stirred at 60° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was washed successively with water and ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was washed with ethyl acetate/diisopropyl ether to give the title compound (68.1 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed successively with water and ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. washthe obtained solid was washed with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-c18e74b3a66a42e18a369d866fe97369
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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