Dimethyl Sulfoxide → 5-(2-Methoxyethyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 593084Notes

Reaction equation

HRID 593084 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]([CH2:9]Cl)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.[CH3:14][O:15][CH2:16][CH2:17][NH2:18].CS(C)=O>C(OCC)(=O)C>[CH3:14][O:15][CH2:16][CH2:17][N:18]1[CH2:2][CH2:3][N:4]2[N:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[C:8]2[CH2:9]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 80182-MethoxyethylamineHCID 866845401-(2-Bromoethyl)-5-(chloromethyl)-3-nitro-1H-pyrazole

Product 1

HCID 866839905-(2-Methoxyethyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineYield 75.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A microwave vial equipped with a magnetic stirrer was charged with 296c (2.67 g, 10.0 mmol), 2-methoxyethanamine (2.25 g, 30.0 mmol), and DMSO (14 mL). The reaction mixture was heated at 120° C. under microwave irradiation for 1.0 h. It was cooled to room temperature and diluted with ethyl acetate (40 mL). The mixture was washed with water (3×15 mL). The organic layer was dried and filtered. The filtrate was concentrated under pressure and the residual was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 296d (1.7 g, 75%) as a yellow solid. MS-ESI: [M+H]+ 227.0

Workup

  1. customA microwave vial equipped with a magnetic stirrer
  2. temperatureIt was cooled to room temperature
  3. washThe mixture was washed with water (3×15 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under pressure
  7. customthe residual was purified by silica-gel column chromatography
  8. washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-736714ff69024d5d94bb993e22c17bba
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

Loading…