O-(propan-2-yl)hydroxylamine hydrochloride → HCID 67505846, compound

HRID 2105504Notes

Reaction equation

HRID 2105504 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[N:10]=[CH:9][C:8]=1[NH:17][C:18](=O)[CH2:19][CH2:20][CH2:21][CH3:22])(=O)=O.Cl.[CH:27]([O:30][NH2:31])([CH3:29])[CH3:28]>C(O)(C)C>[CH2:19]([C:18]1[N:31]([O:30][CH:27]([CH3:29])[CH3:28])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 12696235O-(propan-2-yl)hydroxylamine hydrochlorideHCID 86625950HCID 86625950, compound

Product 1

HCID 67505846HCID 67505846, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3-(pentanoylamino)[1,5]naphthyridin-4-yl trifluoromethanesulfonate (2.7 g, 7.2 mmol), O-isopropylhydroxylamine hydrochloride (1.1 g, 9.9 mmol), and isopropanol (50 mL) was heated at reflux for six hours, allowed to cool to room temperature, stirred overnight, and concentrated under reduced pressure. The residue was stirred with dichloromethane (100 mL) and saturated aqueous sodium carbonate (50 mL) for 15 minutes. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product (2.3 g) was purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 2 mL of aqueous ammonium hydroxide per liter of eluent) to provide 0.40 g of 2-butyl-1-isopropoxy-1H-imidazo[4,5-c][1,5]naphthyridine as an oil.

Workup

  1. temperatureat reflux for six hours
  2. concentrationconcentrated under reduced pressure
  3. stirringThe residue was stirred with dichloromethane (100 mL) and saturated aqueous sodium carbonate (50 mL) for 15 minutes
  4. customThe organic layer was separated
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product (2.3 g) was purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 2 mL of aqueous ammonium hydroxide per liter of eluent)

Sources & evidence

ORD record
ord-290c3d7a633e47d48883e21e521a7998
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

Loading…