Isopropylamine → HCID 59828239, compound

HRID 512464Notes

Reaction equation

HRID 512464 reaction equation
[F:1][CH:2]([F:13])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([OH:12])=O)=[CH:5][CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:26]([NH2:29])([CH3:28])[CH3:27]>O1CCCC1>[F:13][CH:2]([F:1])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([NH:29][CH:26]([CH3:28])[CH3:27])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 685011126-(Difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 59828239HCID 59828239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After dissolution of 200 mg (1.1 mmol) of 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid in 25 ml of tetrahydrofuran and addition of 206 mg (1.3 mmol) of N,N-carbonyldiimidazole, the mixture was stirred initially at room temperature for 30 min and then under reflux for 30 min. A solution of 66 mg (1.1 mmol) of isopropylamine in 5 ml of tetrahydrofuran was then added dropwise, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness, the residue was then taken up in ethyl acetate and the mixture was washed with 2N hydrochloric acid and water, dried and concentrated. Purification by column chromatography gave 150 mg (61% of theory) of a colorless 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. washthe mixture was washed with 2N hydrochloric acid and water
  6. customdried
  7. concentrationconcentrated
  8. customPurification by column chromatography
  9. customgave 150 mg (61% of theory) of a colorless powder

Sources & evidence

ORD record
ord-4a69a0deb2f54b83b4a09f5744904887
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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