HCID 58076143, compound → HCID 70983445, compound

HRID 1747715Notes

Reaction equation

HRID 1747715 reaction equation
Br[C:2]1[N:3]=[C:4]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[N:6]2.[Cu][C:20]#[N:21]>CS(C)=O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][C:4]1[N:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:10]2=[C:2]([C:20]#[N:21])[N:3]=1

Participants

4

Reactant 2

HCID 58076143HCID 58076143, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 70983445HCID 70983445, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
170 °C

Procedure

1.00 g (3.266 mmol) of the compound obtained in Example 5A were initially charged in dry DMSO (25 ml), 1.170 g (13.066 mmol) of copper(I) cyanide were then added and, with stirring, the mixture was heated to 170° C. for 3.5 h. The mixture was filtered through Celite, and the filter cake was washed with ethyl acetate and tetrahydrofuran. The filtrate was then extracted four times with a mixture of saturated aqueous ammonium chloride solution/aqueous ammonia (33%) (3:1, v/v) and washed once with saturated aqueous sodium chloride solution. The phases were separated and the organic phase was dried with sodium sulfate, filtered and concentrated. The residue was treated with ethanol in an ultrasonic bath, and water was then added. The precipitate formed was filtered off, washed with ethanol and then dried under high vacuum. This gave 586 mg of the target compound (71% of theory).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with ethyl acetate and tetrahydrofuran
  3. extractionThe filtrate was then extracted four times
  4. additionwith a mixture of saturated aqueous ammonium chloride solution/aqueous ammonia (33%) (3:1, v/v)
  5. washwashed once with saturated aqueous sodium chloride solution
  6. customThe phases were separated
  7. dry with materialthe organic phase was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe residue was treated with ethanol in an ultrasonic bath
  11. additionwater was then added
  12. customThe precipitate formed
  13. filtrationwas filtered off
  14. washwashed with ethanol
  15. customdried under high vacuum

Sources & evidence

ORD record
ord-9b65cefec65640e8873f4b4fcb6dd4e3
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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