Diethylamine → HCID 59828240, compound

HRID 512476Notes

Reaction equation

HRID 512476 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:19](O)=[O:20])[C:5](=[O:18])[NH:6][C:7]=1[C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:19]([N:36]([CH2:37][CH3:38])[CH2:34][CH3:35])=[O:20])[C:5](=[O:18])[NH:6][C:7]=1[C:8]([F:16])([F:17])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 86624092HCID 86624092, compound

Product 1

HCID 59828240HCID 59828240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolution of 355 mg (1.04 mmol) of 5-chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid in 30 ml tetrahydrofuran and addition of 337 mg (2.08 mmol) of N,N-carbonyldiimidazole, the mixture was stirred initially at room temperature for 30 min and then under reflux for 30 min. 152 mg (0.22 ml, 2.08 mmol) of diethylamine were then added, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness and then taken up in dichloromethane, washed with 1N hydrochloric acid and water, dried and concentrated. This gave 300 mg (72% of theory) of the product.

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 1N hydrochloric acid and water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b50a48c4d46408f97dd0713dfd14acb
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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