Methyl morpholine oxide → HCID 25120537, compound

HRID 1893462Notes

Reaction equation

HRID 1893462 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[C:13]([CH:16]=C)=[CH:14][N:15]=[C:8]1[C:7]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])=[N:6]2.C[N+]1([O-])CC[O:29]CC1.I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O.O.[Os](=O)(=O)(=O)=O>[OH:22][CH2:21][CH2:20][CH2:19][NH:18][C:7]1[C:8]2[N:9]([C:13]([CH:16]=[O:29])=[CH:14][N:15]=2)[C:10]2[C:5]([N:6]=1)=[CH:4][C:3]([C:2]([F:23])([F:1])[F:24])=[CH:12][CH:11]=2

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 25070424HCID 25070424, compound

Product 1

HCID 25120537HCID 25120537, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
30 °C

Procedure

To a suspension of 3-{[7-(trifluoromethyl)-1-vinylimidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol (33 mg, 0.099 mmol) in acetone-water (9:1, 1 mL), was added osmium tetroxide (2.5% wt. in t-BuOH, 53 mg, 0.05 mmol) and 4-methylmorpholine 4-oxide (25 mg, 0.20 mmol). The reaction mixture was stirred for 4 days at 30° C. under argon, and then a suspension of sodium periodate (85 mg, 0.40 mmol) in water (500 μL) was added. The mixture was stirred for one day at 30° C. under argon. Then it was filtered, washed with an aqueous saturated solution of Na2SO3 and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, concentrated in vacuo, filtered, concentrated to give, after purification by preparative TLC (dichloromethane/methanol 9/1), the title compound (24 mg, 70%) as a pale yellow solid.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for one day at 30° C. under argon
  3. filtrationThen it was filtered
  4. washwashed with an aqueous saturated solution of Na2SO3
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give
  11. customafter purification by preparative TLC (dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-f0de028556d04f74a1f6444b34955023
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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