Potassium Carbonate → HCID 86690911, compound

HRID 714618Notes

Reaction equation

HRID 714618 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:9](=[O:12])[NH:10][N:11]=2)=[CH:4][CH:3]=1.Br[CH2:22][C:23]#[N:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:9](=[O:12])[N:10]([CH2:22][C:23]#[N:24])[N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 58012116HCID 58012116, compound

Product 1

HCID 86690911HCID 86690911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 250 mg (0.81 mmol) of 5-(5-chloro-2-thienyl)-4-(2-fluorobenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one [preparation according to WO 2007/134862 Example 154A], 67 μl (0.97 mmol) of bromoacetonitrile and 223 mg (1.61 mmol) of potassium carbonate was stirred in 8 ml of dry DMF at an oil bath temperature of 100° C. for 1 h. After cooling, the mixture was filtered through kieselguhr, the filtrate was concentrated under reduced pressure and the residue was partitioned between MTBE and water. The organic phase was washed successively with 10 ml of water and 10 ml of saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gave 258 mg (92% of theory) of the target compound as a slightly yellowish solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through kieselguhr
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between MTBE and water
  5. washThe organic phase was washed successively with 10 ml of water and 10 ml of saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-968cfc33146447d8b8a18bffd5ca1665
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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