Dimethylformamide → Ethyl 1-(4-t-butylamino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 610194Notes

Reaction equation

HRID 610194 reaction equation
CN(C)C=O.[C:6]([NH:10][C:11]1[C:16]([F:17])=[C:15]([F:18])[N:14]=[C:13]([NH:19][CH:20]=[C:21]([C:27](=[O:38])[C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([Cl:36])[C:29]=2F)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]=1[F:39])([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[C:6]([NH:10][C:11]1[C:16]([F:17])=[C:15]([F:18])[N:14]=[C:13]([N:19]2[C:29]3[C:28](=[CH:33][C:32]([F:34])=[C:31]([F:35])[C:30]=3[Cl:36])[C:27](=[O:38])[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20]2)[C:12]=1[F:39])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 178471971HCID 178471971, compound

Product 1

HCID 22121213Ethyl 1-(4-t-butylamino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 114.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 6 ml of N,N-dimethyl-formamide solution of 1.14 g of ethyl 3-[(4-t-butylamino-3,5,6-trifluoropyridin-2-yl)amino]-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate was added 700 mg of potassium carbonate, and the mixture was stirred at room temperature for 3.5 hours. The reaction solution was poured into ice water, and ethyl acetate was added for extraction. The organic layer was separated and dried over magnesium sulfate, and solvent was distilled off. The solid content was collected by filtration to obtain 1.25 g of the title compound as a colorless powder.

Workup

  1. additionwas added for extraction
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate, and solvent
  4. distillationwas distilled off
  5. filtrationThe solid content was collected by filtration

Sources & evidence

ORD record
ord-bfdecb8c2777420fafd7d37c32f549c5
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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