Methyl iodide → HCID 58386683, compound

HRID 74538Notes

Reaction equation

HRID 74538 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][C:4]2[CH:15]=[N:16][NH:17][C:3]1=2.[H-].[Na+].I[CH3:22]>CN(C=O)C>[CH3:22][N:17]1[C:3]2[C:2]([CH3:18])([CH3:1])[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:5][C:4]=2[CH:15]=[N:16]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 37818370tert-Butyl 7,7-dimethyl-1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate

Product 1

HCID 58386683HCID 58386683, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.10 g (8.36 mmol) tert. butyl 7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylate were placed in 25 mL DMF. While cooling with ice, 350 mg (8.75 mmol) sodium hydride (55%) were added. The reaction mixture was stirred for 30 min, then 0.540 mL (8.67 mmol) iodomethane were added and the mixture was stirred for 1 h at 0° C. The reaction mixture was concentrated to dryness by rotary evaporation and the residue was mixed with water and extracted with EtOAc. The organic phase was dried, filtered and concentrated to dryness by rotary evaporation. The residue was purified by HPLC. The product-containing fractions were combined and organic solvent was eliminated by rotary evaporation. The aqueous residue was extracted with DCM. The organic phase was dried, filtered and concentrated to dryness by rotary evaporation.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 1 h at 0° C
  3. concentrationThe reaction mixture was concentrated to dryness by rotary evaporation
  4. additionthe residue was mixed with water
  5. extractionextracted with EtOAc
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness by rotary evaporation
  9. customThe residue was purified by HPLC
  10. customorganic solvent was eliminated by rotary evaporation
  11. extractionThe aqueous residue was extracted with DCM
  12. customThe organic phase was dried
  13. filtrationfiltered
  14. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-16864c26d23144a79b6ffdda67a79165
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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