1,1'-Carbonyldiimidazole → HCID 59828244, compound

HRID 512455Notes

Reaction equation

HRID 512455 reaction equation
[Cl:1][C:2]([F:14])([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.Cl.[CH3:28][O:29][C:30](=[O:33])[CH2:31][NH2:32]>O1CCCC1>[Cl:1][C:2]([F:14])([F:13])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([NH:32][CH2:31][C:30]([O:29][CH3:28])=[O:33])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 122755Glycine methyl ester hydrochlorideHCID 22113416HCID 22113416, compound

Product 1

HCID 59828244HCID 59828244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

300 mg (1.34 mmol) of 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid were dissolved in 5 ml of tetrahydrofuran, 435 mg (2.68 mmol) of N,N-carbonyldiimidazole were added and the mixture was stirred initially at room temperature for 30 min and then under reflux for 30 min. A mixture of 168 mg (1.34 mmol) of glycine methyl ester hydrochloride in 3 ml of tetrahydrofuran was then added, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness, the residue was taken up in ethyl acetate and the solution was washed with 1N hydrochloric acid and water, dried and concentrated. This gave 92 mg (23% of theory) of a light-brown powder.

Workup

  1. temperatureunder reflux for 30 min
  2. additionwas then added
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 2 h
  5. customThe solution was evaporated to dryness
  6. washthe solution was washed with 1N hydrochloric acid and water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8e3057f0b3654857a76eb4d7a510f1f3
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

Loading…