Methyl iodide → N-(1-((1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79368Notes

Reaction equation

HRID 79368 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[C:26]([OH:32])=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[N:4]=1)[CH3:2].CI.[C:35]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:35][N:27]1[C:28]([CH3:31])=[CH:29][CH:30]=[C:25]([CH2:24][N:5]2[C:6]3[C:11](=[C:10]([NH:12][C:13]([C:15]4[N:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]5=[N:17][CH:16]=4)=[O:14])[CH:9]=[CH:8][CH:7]=3)[C:3]([CH2:1][CH3:2])=[N:4]2)[C:26]1=[O:32]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178437933HCID 178437933, compound

Product 1

HCID 67260935N-(1-((1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 31.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3-ethyl-1-((2-hydroxy-6-methylpyridin-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (18.3 mg, 0.0429 mmol) and methyl iodide (2.68 μL, 0.0429 mmol) with K2CO3 (17.8 mg, 0.129 mmol) in DMF (3 mL) was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and water. The aqueous phase was extracted 3 times with EtOAc. The organic phases were combined and washed with brine. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (10:1 DCM/MeOH) to provide the final product (6 mg). MS (ES+APCI) m/z=441 (M+H).

Workup

  1. extractionThe aqueous phase was extracted 3 times with EtOAc
  2. washwashed with brine
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel chromatography (10:1 DCM/MeOH)

Sources & evidence

ORD record
ord-a31cf364d06d411494268b9e64f1b1fe
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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