Cesium carbonate → 1-({5-chloro-1-[(3R)-1,1-dioxidotetrahydrothiophen-3-yl]-1H-benzimidazol-2-yl}methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine

HRID 1500862Notes

Reaction equation

HRID 1500862 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C@H:11]3[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12]3)[C:7]([CH2:9]Cl)=[N:8][C:4]=2[CH:3]=1.[CH3:20][S:21]([C:24]1[C:32]2[C:27](=[CH:28][N:29]=[CH:30][CH:31]=2)[NH:26][N:25]=1)(=[O:23])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C@@H:11]3[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12]3)[C:7]([CH2:9][N:26]3[C:27]4=[CH:28][N:29]=[CH:30][CH:31]=[C:32]4[C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[N:25]3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 89933231(S)-3-(5-Chloro-2-(chloromethyl)-1H-benzo[d]imidazol-1-yl)tetrahydrothiophene 1,1-dioxideHCID 178504858HCID 178504858, compound

Product 1

HCID 729490861-({5-chloro-1-[(3R)-1,1-dioxidotetrahydrothiophen-3-yl]-1H-benzimidazol-2-yl}methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridineYield 34.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 5-chloro-2-chloromethyl-1-((S)-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-1H-benzoimidazole(115 mg, 0.36 mmol), 3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (60 mg, 0.36 mmol) and Cs2CO3 (236 mg, 0.76 mmol) in 4 mL of DMF was stirred at room temperature for 1 h. The mixture was filtered, the filtrate was collected, then to the filtrate was added oxone (300 mg). The mixture was stirred for 4 hrs and purified by prep-HPLC to give the product (60 mg, yield: 34.6%) as an off-white solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was collected
  3. additionto the filtrate was added oxone (300 mg)
  4. stirringThe mixture was stirred for 4 hrs
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-07819f0d2b044884b048cc0bfc6f558a
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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