Sodium Iodide → HCID 117988236, compound

HRID 2206216Notes

Reaction equation

HRID 2206216 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:17]3[C:18]([O:22][CH3:23])=[N:19][CH:20]=[CH:21][C:16]=3[N:15]([C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])[N:14]=2)[CH:8]=1)(=O)=O.Cl.[CH3:33][NH:34][CH3:35].[I-].[Na+].C(=O)([O-])O.[Na+]>CN(C=O)C.C(N(CC)CC)C>[F:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:24]=1[N:15]1[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH3:23])[C:17]=2[C:13]([C:9]2[CH:8]=[C:7]([CH2:6][N:34]([CH3:35])[CH3:33])[CH:12]=[CH:11][CH:10]=2)=[N:14]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 117988223HCID 117988223, compound

Product 1

HCID 117988236HCID 117988236, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzyl methanesulfonate (75 mg), dimethylamine hydrochloride (79 mg) and sodium iodide (29 mg) in DMF (1 mL) was added triethylamine (0.135 mL), and the mixture was stirred at 90° C. for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane) to give the title compound (62 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fad65ed84c94468db253a75733c7adfa
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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