Methyl iodide → 5-bromo-N-(2-hydroxyethyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

HRID 58045Notes

Reaction equation

HRID 58045 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[CH:3]=1.IC.[C:17](=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH3:17])[CH:5]=[C:4]([C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 897817505-bromo-N-(2-hydroxyethyl)-6-oxo-1,6-dihydropyridine-3-carboxamide

Product 1

HCID 897947825-bromo-N-(2-hydroxyethyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-bromo-N-(2-hydroxyethyl)-6-oxo-1,6-dihydropyridine-3-carboxamide (400 mg, 1.532 mmol), iodomethane (0.114 mL, 1.839 mmol), and potassium carbonate (212 mg, 1.532 mmol) in DMSO (5 mL) was stirred at room temperature overnight. The reaction mixture was subsequently filtered and purified via preparative HPLC, eluting with a gradient of 1-30% ACN in H2O (containing 10 mM NH4HCO3) to give the title compound.

Workup

  1. filtrationThe reaction mixture was subsequently filtered
  2. custompurified via preparative HPLC
  3. washeluting with a gradient of 1-30% ACN in H2O (containing 10 mM NH4HCO3)

Sources & evidence

ORD record
ord-f7b48de156a34586a0e3a1ae6d251c59
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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