Cesium carbonate → HCID 89923994, compound

HRID 1500922Notes

Reaction equation

HRID 1500922 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH:11]3[CH2:15][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[C:13](=[O:25])[CH2:12]3)[C:7]([CH2:9]Cl)=[N:8][C:4]=2[CH:3]=1.[CH3:28][S:29]([C:32]1[C:40]2[C:35](=[CH:36][N:37]=[CH:38][CH:39]=2)[NH:34][N:33]=1)(=[O:31])=[O:30].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.CCOC(C)=O>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH:11]3[CH2:15][N:14]([CH2:16][C:17]4[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=4)[C:13](=[O:25])[CH2:12]3)[C:7]([CH2:9][N:34]3[C:35]4=[CH:36][N:37]=[CH:38][CH:39]=[C:40]4[C:32]([S:29]([CH3:28])(=[O:30])=[O:31])=[N:33]3)=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 89924058HCID 89924058, compoundHCID 178504858HCID 178504858, compound

Product 1

HCID 89923994HCID 89923994, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-chloro-2-(chloromethyl)-1H-benzimidazol-1-yl]-1-(4-methoxybenzyl)pyrrolidin-2-one (294 mg, 1.492 mmol) in 50 mL of DMF was added 3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (722 mg, 1.791 mmol) and Cs2CO3 (584 mg, 2.985 mmol). The resulting mixture was stirred at RT for 4 hours, then diluted with 40 mL of H2O and EtOAc. The separated aqueous phase was extracted with EtOAc (15 mL×3). The combined organic phases were washed with 30 mL of brine, and then dried over Na2SO4, then filtered and concentrated in vacuo. The residue was purified by column chromatography (DCM: MeOH=20:1) to give 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 as a solid.

Workup

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

Sources & evidence

ORD record
ord-79216f80e1824056a9fdc3d0bf317e1f
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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