1-Hydroxybenzotriazole → 5-Bromo-N-methoxy-N-methylpicolinamide

HRID 1520292Notes

Reaction equation

HRID 1520292 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.O.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:10])=[N:6][CH:7]=1

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 629527015-Bromo-N-methoxy-N-methylpicolinamideYield 75.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromopyridine-2-carboxylic acid (3.0 g), N,O-dimethylhydroxylamine hydrochloride (2.9 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.69 g), 1-hydroxybenzotriazole (4.01 g), N,N-diisopropylethylamine (12.97 mL), 4-dimethylaminopyridine (0.181 g) and DMF (37.1 mL) was stirred at room temperature for 5 hr, and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.76 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-83b717d49d7f4f9f857b949ab17dbea9
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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