Ammonium Chloride → HCID 67123879, compound

HRID 1500757Notes

Reaction equation

HRID 1500757 reaction equation
C[O-].[Na+].[N:4]1[N:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]2=[C:6]([C:13]#[N:14])[CH:5]=1.[Cl-:15].[NH4+:16]>CO.C(OCC)(=O)C>[ClH:15].[N:4]1[N:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]2=[C:6]([C:13](=[NH:16])[NH2:14])[CH:5]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide2×HCID 67123869HCID 67123869, compound

Product 1

HCID 67123879HCID 67123879, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Freshly prepared sodium methoxide (0.44 g, 8.1 mmol) was added to a suspension of pyrazolo[1,5-a]pyrazine-3-carbonitrile (Preparation 24b, 6.09 g, 42.3 mmol) in anhydrous methanol (350 mL) and the mixture was stirred at ambient temperature. After 20 hours, further sodium methoxide (0.44 g, 8.1 mmol) was added and the reaction mixture was stirred for a further 48 hours. Ammonium chloride (3.91 g, 73.1 mmol) was added and the mixture was stirred and heated to 70° C. in a sealed tube. After 3 days, the mixture was concentrated to dryness to give a solid which was suspended in ethyl acetate and stirred overnight. The precipitate was filtered and dried in vacuo to give the crude title compound (8.50 g, >100%) as a white solid which was used in the next synthetic step without further purification.

Workup

  1. stirringthe reaction mixture was stirred for a further 48 hours
  2. stirringthe mixture was stirred
  3. temperatureheated to 70° C. in a sealed tube
  4. waitAfter 3 days
  5. concentrationthe mixture was concentrated to dryness
  6. customto give a solid which
  7. stirringstirred overnight
  8. filtrationThe precipitate was filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-155566ffedae403fb4ed3dbbcbad365b
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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