2-Nitro-5-(2,2,2-trifluoroethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 5-(2,2,2-Trifluoroethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 407727Notes

Reaction equation

HRID 407727 reaction equation
[N+:1]([C:4]1[CH:17]=[C:7]2[CH2:8][N:9]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:11][N:6]2[N:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[F:16][C:13]([F:14])([F:15])[CH2:12][N:9]1[CH2:10][CH2:11][N:6]2[N:5]=[C:4]([NH2:1])[CH:17]=[C:7]2[CH2:8]1

Participants

5

Reactant 2

HCID 866839962-Nitro-5-(2,2,2-trifluoroethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 866839975-(2,2,2-Trifluoroethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 134a (390 mg, 1.56 mmol) in ethanol (20 mL) was added Pd/C (about 200 mg). The reaction was charged with hydrogen gas (via balloon) and stirred at room temperature for 2 h. After reaction was complete, the mixture was filtered through a plug of CELITE®. The filtrate was concentrated under reduced pressure to afford 134b as a yellow solid (308 mg, 90%), which was used in the next step without further purification. MS-ESI: [M+H]+ 221.1

Workup

  1. customAfter reaction
  2. filtrationthe mixture was filtered through a plug of CELITE®
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-92e48791c0bf4952a648a520e671c6f7
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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