2-Methoxyethylamine → HCID 59828236, compound

HRID 512454Notes

Reaction equation

HRID 512454 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.[CH3:27][O:28][CH2:29][CH2:30][NH2:31]>O1CCCC1>[Cl:1][C:2]([F:14])([F:13])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([NH:31][CH2:30][CH2:29][O:28][CH3:27])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22113416HCID 22113416, compound

Product 1

HCID 59828236HCID 59828236, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

500 mg (2.2 mmol) of 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid were dissolved in 10 ml of tetrahydrofuran, 508 mg (3.1 mmol) of N,N-carbonyldiimidazole were added and the mixture was then stirred initially at room temperature for 30 min and then under reflux for min. A solution of 202 mg (2.7 mmol) of 2-methoxyethylamine in 2 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 taken up in ethyl acetate and the solution was washed with 1N hydrochloric acid and water, dried and concentrated. This gave 360 mg (54% of theory) of a light-brown powder.

Workup

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

Sources & evidence

ORD record
ord-e5511c1a9ecc4e9b9efc468fb38b2efd
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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