Water → HCID 66728128, compound

HRID 573288Notes

Reaction equation

HRID 573288 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:14]=[C:13]([C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]([CH2:24][CH3:25])[N:16]=2)[CH:12]=[N:11]1.CI.[C:28]([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH2:24]([N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[C:15]([C:13]2[CH:12]=[N:11][N:10]([C:2]3[N:1]([CH3:28])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH:14]=2)=[N:16]1)[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66727975HCID 66727975, compound

Product 1

HCID 66728128HCID 66728128, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[(1-(1H-benzo[d]imidazol-2-yl)-1H-pyrazol-4-yl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine (8 mg), MeI (2.278 μL) and Cs2CO3 (15.83 mg) in DMF (2 mL) was stirred at room temperature for 3 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). Crystallization from AcOEt/hexane gave the title compound (4.80 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. customCrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-f921f679cf804a63a2c190c4ec8eefb1
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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