Methanesulfonyl chloride → N-[2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]ethyl]methanesulfonamide

HRID 42604Notes

Reaction equation

HRID 42604 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:9]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:10]2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:5]1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[C:11]3[C:6](=[N:5][N:4]([CH2:3][CH2:2][NH:1][S:34]([CH3:33])(=[O:36])=[O:35])[CH:12]=3)[N:7]=[C:8]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 670135732-(2-Aminoethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Product 1

HCID 67015083N-[2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]ethyl]methanesulfonamideYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 2-(2-aminoethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (0.06 g, 0.15 mmol, obtained in example 90) and DMAP (0.001 g, 0.0058 mmol) in pyridine (0.6 mL), methanesulfonyl chloride (0.017 mL, 0.22 mmol) was added under argon atmosphere and cooled with an ice bath (0.017 mL, 0.22 mmol). This was stirred overnight at room temperature. The solvent was concentrated. The residue was dissolved in CHCl3 and saturated NaHCO3 was added. The phases were separated. The organic phase was dried over Na2SO4 and concentrated. The crude product obtained was purified by chromatography on silica gel using EtOAc as solvent, and 70 mg of the title compound was obtained (yield: 95%).

Workup

  1. temperaturecooled with an ice bath (0.017 mL, 0.22 mmol)
  2. concentrationThe solvent was concentrated
  3. dissolutionThe residue was dissolved in CHCl3
  4. additionsaturated NaHCO3 was added
  5. customThe phases were separated
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product obtained
  9. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8ff893196953441ea206295467c2b0c2
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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