5-(3-Methoxypropyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 5-(3-Methoxypropyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 593114Notes

Reaction equation

HRID 593114 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([N+:15]([O-])=O)[CH:14]=[C:8]2[CH2:7]1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([NH2:15])[CH:14]=[C:8]2[CH2:7]1

Participants

5

Reactant 2

HCID 866845565-(3-Methoxypropyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 866845575-(3-Methoxypropyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 309a (300 mg, 1.25 mmol) in ethanol (20 mL) was added Pd/C (10%, 30 mg). The reaction was charged with hydrogen gas (via balloon) and stirred at room temperature for 1 h. After the reaction was complete, the mixture was filtered through a plug of CELITE®. The filtrate was concentrated under reduced pressure to afford 309b as a yellow solid (250 mg, 92%), which was used without further purification in the next step. MS-ESI: [M+H]+ 211.3

Workup

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

Sources & evidence

ORD record
ord-21871bb041c04aca93ffa03a7aace87b
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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