Hydroxylamine → HCID 59743375, compound

HRID 1946979Notes

Reaction equation

HRID 1946979 reaction equation
F[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=1)=O.[NH2:20][OH:21].C1CCN2C(=NCCC2)CC1>C(O)C.CCOC(C)=O>[CH3:9][O:8][C:7]1[C:2]2[O:21][N:20]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=3)[C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59743359HCID 59743359, compound

Product 1

HCID 59743375HCID 59743375, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-fluoro-3-methoxy-phenyl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone (1 g, 3.59 mmol) and hydroxylamine (50% in water, 1.5 mL) in ethanol was heated to reflux overnight. The resulting mixture was cooled to RT, diluted with EtOAc and then concentrated under reduced pressure. The residue was dissolved in THF and DBU (0.84 mL, 5.6 mmol) was added, the resulting mixture was heated to 150° C. in a microwave reactor for 30 min. The reaction mixture was then concentrated under reduced pressure and the residue was purified by flash chromatography (hexane/EtOAc, 95/5) to give 458 mg of 7-methoxy-3-(2-methylsulfanylpyrimidin-4-yl)-benzo[d]isoxazole.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in THF
  5. temperaturethe resulting mixture was heated to 150° C. in a microwave reactor for 30 min
  6. concentrationThe reaction mixture was then concentrated under reduced pressure
  7. customthe residue was purified by flash chromatography (hexane/EtOAc, 95/5)

Sources & evidence

ORD record
ord-707d954d092d4cb39b268edff1d5697c
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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