Water → HCID 86688963, compound

HRID 573280Notes

Reaction equation

HRID 573280 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH:15]=[C:14]([C:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]([CH2:25][CH3:26])[N:17]=2)[CH:13]=[CH:12][C:11]1=[O:27].CI.[C:30]([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH2:25]([N:18]1[C:19]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[C:16]([C:14]2[CH:13]=[CH:12][C:11](=[O:27])[N:10]([C:2]3[N:1]([CH3:30])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH:15]=2)=[N:17]1)[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86688964HCID 86688964, compound

Product 1

HCID 86688963HCID 86688963, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(1H-benzimidazol-2-yl)-5-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-2(1H)-one (20 mg), MeI (11.95 mg) and Cs2CO3 (36.6 mg) in DMF (1 mL) was stirred at room temperature for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) and crystallized from hexane/AcOEt to give the title compound (12 mg).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
  5. customcrystallized from hexane/AcOEt

Sources & evidence

ORD record
ord-75e13b474f8048fc8580ef4a78b22597
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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