Water → 5-hydroxy-N-methoxy-N-methylpicolinamide

HRID 626150Notes

Reaction equation

HRID 626150 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN([C:14]([O:18][N:19]1N=NC2C=CC=N[C:20]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CONC.O>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:19]([O:18][CH3:14])[CH3:20])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 866889815-hydroxy-N-methoxy-N-methylpicolinamideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-hydroxypicolinic acid (1.0 eq), HATU (1.2 eq) and N-methoxymethanamine hydrochloride (1.2 eq) in dry DMF was added DIEtOAc (2.5 eq) dropwise at rt. The mixture was then stirred overnight at rt. After addition with water, the mixture was extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (87% yield).

Workup

  1. additionwas added DIEtOAc (2.5 eq) dropwise at rt
  2. extractionthe mixture was extracted with CH2Cl2
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-924bf59f75734bb8a1190c44dcd8996f
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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