Water → HCID 66672506, compound

HRID 1877524Notes

Reaction equation

HRID 1877524 reaction equation
[C:1]([C:3]1[C:8](F)=[CH:7][C:6]([F:10])=[CH:5][N:4]=1)#[N:2].NCCC1C=[CH:18][CH:17]=[CH:16][N:15]=1.[C:20](=O)([O-])[O-].[K+].[K+].[OH2:26]>CS(C)=O.C(OCC)(=O)C>[C:1]([C:3]1[C:8]([NH:15][CH2:16][C:17]([OH:26])([CH3:18])[CH3:20])=[CH:7][C:6]([F:10])=[CH:5][N:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 759192-PyridineethanamineHCID 27832532-Cyano-3,5-difluoropyridine

Product 1

HCID 66672506HCID 66672506, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

1.8 g of 2-cyano-3,5-difluoropyridine, 1.375 g of 2-(2-aminoethyl)pyridine and 3.552 g of potassium carbonate in 27 ml of dimethyl sulphoxide are introduced into a 20 ml microwave tube reactor by means of three successive identical operations. The mixture is then heated in a microwave for 1 hour at 115° C. The reaction medium is run into 100 ml of water and 200 ml of ethyl acetate. The aqueous phase is re-extracted twice with 250 ml of ethyl acetate. The combined organic phases are washed with water and then with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. After purification by flash chromatography on 200 g of silica gel, elution being carried out with a mixture of ethyl acetate and cyclohexane (50/50 by volume), and the first eluted product being recovered, 768 mg of 2-cyano-5-fluoro-3-(2-hydroxy-2-methylpropylamino)pyridine are thus obtained in the form of a beige powder, the characteristic of which is the following:

Workup

  1. extractionThe aqueous phase is re-extracted twice with 250 ml of ethyl acetate
  2. washThe combined organic phases are washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by flash chromatography
  6. washon 200 g of silica gel, elution
  7. additionbeing carried out with a mixture of ethyl acetate and cyclohexane (50/50 by volume)
  8. customthe first eluted product being recovered

Sources & evidence

ORD record
ord-db8a434f472046d4a5813fbb77182303
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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