HCID 89923994, compound → HCID 72948719, compound

HRID 1500923Notes

Reaction equation

HRID 1500923 reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][C:5]2[N:6]([CH:23]3[CH2:27][N:26](CC4C=CC(OC)=CC=4)[C:25](=[O:37])[CH2:24]3)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1>CC#N.O.CCOC(C)=O>[Cl:1][C:2]1[CH:39]=[CH:38][C:5]2[N:6]([CH:23]3[CH2:27][NH:26][C:25](=[O:37])[CH2:24]3)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 89923994HCID 89923994, compound

Product 1

HCID 72948719HCID 72948719, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-chloro-2-{[3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridin-1-yl]methyl}-1H-benzimidazol-1-yl)-1-(4-methoxybenzyl)pyrrolidin-2-one (208 mg, 0.37 mmol) in 60 mL of CH3CN and 12 mL of H2O was added (NH4)2Ce(NO3)6 (1.01 g, 1.84 mmol). The resulting mixture was stirred at RT for 6 hours. The solution was diluted with 40 mL of water and 15 mL of EtOAc. The separated aqueous phase was extracted with EtOAc (15 mL×3) and THF (5 mL×3). The combined organic phases were washed with 30 mL of brine, and then dried over Na2SO4, then filtered and concentrated. The residue was purified by column chromatography (DCM: MeOH=20:1) to afford 4-(5-chloro-2-{[3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridin-1-yl]methyl}-1H-benzimidazol-1-yl)pyrrolidin-2-one.

Workup

  1. extractionThe separated aqueous phase was extracted with EtOAc (15 mL×3) and THF (5 mL×3)
  2. washThe combined organic phases were washed with 30 mL of brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (DCM: MeOH=20:1)

Sources & evidence

ORD record
ord-17dd81c1d2ff4bfd8e8d45eb5bad539a
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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