Triethylamine → HCID 117988057, compound

HRID 2206215Notes

Reaction equation

HRID 2206215 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18][CH3:19])[C:12]=2[C:11]([C:20]2[CH:21]=[C:22]([CH2:26][OH:27])[CH:23]=[CH:24][CH:25]=2)=[N:10]1.C(N(CC)CC)C.[CH3:35][S:36]([Cl:39])(=[O:38])=[O:37].C(=O)([O-])O.[Na+]>C1COCC1>[CH3:35][S:36]([O:27][CH2:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:11]2[C:12]3[C:13]([O:18][CH3:19])=[N:14][CH:15]=[CH:16][C:17]=3[N:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[N:10]=2)[CH:21]=1)(=[O:38])=[O:37].[Cl:39][CH2:26][C:22]1[CH:21]=[C:20]([C:11]2[C:12]3[C:13]([O:18][CH3:19])=[N:14][CH:15]=[CH:16][C:17]=3[N:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[N:10]=2)[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 117987900HCID 117987900, compound

Product 2

HCID 117988057HCID 117988057, compoundHCID 117988223HCID 117988223, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)methanol (400 mg) and triethylamine (0.228 mL) in THF (3 mL) was added methanesulfonyl chloride (0.126 mL) at 0° C., and the mixture was stirred overnight at room temperature. 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 (ethyl acetate/hexane) to give 3-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzyl methanesulfonate (386 mg) and 3-(3-(chloromethyl)phenyl)-1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridine (48 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 (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c7613f04909b4233aec0e9cf0231e954
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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