Ethyl formate → 5-Fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile

HRID 340439Notes

Reaction equation

HRID 340439 reaction equation
[CH:1](OCC)=O.[H-].[Na+].C([O:11][CH2:12][CH2:13][F:14])(=O)C.[C:15]([CH2:17][C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)=[NH:19])#[N:16]>C(O)C.CCCCCC>[F:14][C:13]1[C:12](=[O:11])[NH:19][C:18]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[CH:26][CH:25]=[CH:24]3)=[C:17]([C:15]#[N:16])[CH:1]=1

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 10016Ethanol, 2-fluoro-, 1-acetateHCID 24758Sodium hydrideHCID 178511140HCID 178511140, compound

Product 1

HCID 686063515-Fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8058HexaneSolvent

Procedure

Ethyl formate (16.1 ml) was added to a hexane (40 ml) suspension containing sodium hydride (60% in oil, 2.4 g) at room temperature, and then fluoroethyl acetate (3.86 ml) was added dropwise under ice cooling, followed by stirring at room temperature for 15 minutes. Ethanol (50 ml) was added to the reaction mixture, and then an ethanol (50 ml) solution containing 2-cyano-N-(quinolin-6-yl)acetamidine (4.20 g) was added dropwise, followed by stirring at 80° C. for 2 hours. The reaction mixture was cooled to room temperature. Then, solid matter was collected by filtration and washed with ethyl acetate, and a yellow solid of 5-fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile (3.71 g) was thus obtained.

Workup

  1. additionwas added dropwise
  2. stirringby stirring at 80° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThen, solid matter was collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-0af78f720882434f8794c4e806fad912
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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