Cesium carbonate → HCID 72949084, compound

HRID 1500880Notes

Reaction equation

HRID 1500880 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([C@H:23]3[CH2:27][CH2:26][NH:25][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.FC(F)(F)S(O[CH2:36][C:37]([F:40])([F:39])[F:38])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([C@H:23]3[CH2:27][CH2:26][N:25]([CH2:36][C:37]([F:40])([F:39])[F:38])[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:20])=[O:21])=[N:11]3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 118114479HCID 118114479, compound

Product 1

HCID 72949084HCID 72949084, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-1-((5-chloro-1-(pyrrolidin-3-yl)-1H-benzo[d]imidazol-2-yl)methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (120 mg, 0.28 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (64 mg, 0.28 mmol) and Cs2CO3 (182 mg, 0.56 mmol) in 5 mL of DMF was stirred overnight. The mixture was filtered and purified by prep-HPLC to give 1-({5-chloro-1-[(3S)-(1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-1H-benzimidazol-2-yl}methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (30 mg, yield: 21%) as an off-white solid.

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-665075c0dbc049ccbccd135c49d297b9
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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