Water → 6-Fluoro-N-methoxy-N-methylpyridine-3-carboxamide

HRID 627491Notes

Reaction equation

HRID 627491 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.[F:13][C:14]1[N:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1.O>ClCCl>[F:13][C:14]1[N:19]=[CH:18][C:17]([C:20]([N:3]([O:4][CH3:5])[CH3:2])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 146236022-Fluoropyridine-5-carbonyl chloride

Product 1

HCID 587671286-Fluoro-N-methoxy-N-methylpyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 250-mL round-bottom flask containing N,O-dimethyl hydroxylamine hydrochloride (3.5 g, 35.9 mmol) and triethylamine (15.0 mL, 108 mmol) was added a solution of 6-fluoropyridine-3-carbonyl chloride (5.70 g, 35.7 mmol, Intermediate 21, step a) in dichloromethane (200 mL) dropwise. The resulting mixture was stirred for 12 hours at room temperature, and 20 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with 2×100 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by chromatography (silica gel column, 100:1 CHCl3/MeOH) to give the title compound as a white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 2×100 mL of dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography (silica gel column, 100:1 CHCl3/MeOH)

Sources & evidence

ORD record
ord-fbec88a765c449fab84ad6c67eaff3c0
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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