HCID 68011891, compound → HCID 68011870, compound

HRID 920996Notes

Reaction equation

HRID 920996 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[C:5]([C:12]([NH2:14])=O)[N:4]=1>P(Cl)(Cl)(Cl)=O>[F:16][C:2]([F:1])([F:15])[C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[C:5]([C:12]#[N:14])[N:4]=1

Participants

3

Reactant 1

HCID 68011891HCID 68011891, compound

Product 1

HCID 68011870HCID 68011870, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide 10a (100 mg, 0.43 mmol) was dissolved in 5 mL of phosphorus oxychloride. The reaction mixture was heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, added with 10 mL of saturated sodium carbonate solution and extracted with ethyl acetate (25 mL×3). The organic phase was combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain crude 3-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carbonitrile 25a (100 mg) as a brown solid. The product was used directly in the next reaction without purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionadded with 10 mL of saturated sodium carbonate solution
  5. extractionextracted with ethyl acetate (25 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-65d0ea7a27464714a6dfea7b527c2630
Source dataset
uspto-grants-2016_03
Patent number
US09273052B2

Reaction notes

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