1,1'-Carbonyldiimidazole → N-Cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

HRID 512452Notes

Reaction equation

HRID 512452 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[NH:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:27]1([NH2:31])[CH2:30][CH2:29][CH2:28]1>O1CCCC1>[CH:27]1([NH:31][C:8]([C:7]2[C:2](=[O:1])[NH:3][C:4]([C:11]([F:14])([F:13])[F:12])=[CH:5][CH:6]=2)=[O:10])[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 75645CyclobutylamineHCID 27751162-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 59828237N-Cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

600 mg (2.9 mmol) of 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid were dissolved in 5 ml of tetrahydrofuran, 658 mg (4.1 mmol) of N,N-carbonyldiimidazole were added and the mixture was heated initially at room temperature for 30 min and then under reflux for 30 min. A solution of 247 mg (3.5 mmol) of cyclobutylamine in 5 ml tetrahydrofuran was then added dropwise, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness and then taken up in ethyl acetate, washed with 1 N hydrochloric acid and water, dried and concentrated. Purification by column chromatography gave 160 mg (19% of theory) of a light-brown powder.

Workup

  1. temperatureunder reflux for 30 min
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for a further 2 h
  4. customThe solution was evaporated to dryness
  5. washwashed with 1 N hydrochloric acid and water
  6. customdried
  7. concentrationconcentrated
  8. customPurification by column chromatography
  9. customgave 160 mg (19% of theory) of a light-brown powder

Sources & evidence

ORD record
ord-c553715fd82c46a78ba7ad4d4d8652b7
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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