Triethylamine → 5-fluoro-N-methylpyridine-2-carboxamide

HRID 909662Notes

Reaction equation

HRID 909662 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C1C=CC2N(O)N=[N:17][C:15]=2C=1.O.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C.CN.CO>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:17][CH3:15])=[O:10])=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628765-fluoropyridine-2-carboxylic AcidHCID 27960291-Hydroxybenzotriazole hydrateHCID 57454252Monomethylamine methanol

Product 1

HCID 666833945-fluoro-N-methylpyridine-2-carboxamideYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Fluoropyridine-2-carboxylic acid (495 mg, 3.51 mmol) was dissolved in methylene chloride (10 mL), and HOBt•H2O (591 mg, 3.86 mmol), WSCI•HCl (1.35 g, 7.02 mmol), triethylamine (2.44 mL, 17.5 mmol) and 40% methylamine/methanol solution (0.82 mL, 10.5 mmol) were added, followed by stirring for 15 hours. To the reaction solution, water (30 mL) was added, and extraction was carried out twice with methylene chloride (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-50%) to afford the desired compound (490 mg, yield 91%) as a white solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-50%)

Sources & evidence

ORD record
ord-8bd557ac5aa240f0a6c1b28f8ddb6b72
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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