Acetone → HCID 67003853, compound

HRID 2362636Notes

Reaction equation

HRID 2362636 reaction equation
C([N:4]1[CH:8]=[C:7]([C:9]2[N:31]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:12]3=[N:13][CH:14]=[C:15]([Cl:30])[C:16]([C:17]4[S:21][C:20]([C:22]5([O:26][CH2:27][O:28][CH3:29])[CH2:25][CH2:24][CH2:23]5)=[N:19][CH:18]=4)=[C:11]3[CH:10]=2)[CH:6]=[N:5]1)C=C.[CH3:42][C:43]([CH3:45])=[O:44].C[N+]1([O-])CC[O:50]CC1>O.O.[O-][Os]([O-])(=O)=O.[K+].[K+].O>[Cl:30][C:15]1[C:16]([C:17]2[S:21][C:20]([C:22]3([O:26][CH2:27][O:28][CH3:29])[CH2:23][CH2:24][CH2:25]3)=[N:19][CH:18]=2)=[C:11]2[CH:10]=[C:9]([C:7]3[CH:6]=[N:5][N:4]([CH2:42][CH:43]([OH:44])[CH2:45][OH:50])[CH:8]=3)[N:31]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:12]2=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 67002791HCID 67002791, compound

Product 1

HCID 67003853HCID 67003853, compound

Reagents, catalysts & solvents 2

HCID 53393272Potassium osmate(VI) dihydrateCatalystHCID 962WaterSolvent

Procedure

To an ambient solution of 5-(2-(1-allyl-1H-pyrazol-4-yl)-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 14A) (1.5 g, 2.458 mmol) in a solvent mixture of acetone (6.15 mL) and water (2.05 mL) was added potassium osmate (VI) dihydrate (9.06 mg, 0.025 mmol) followed by N-methylmorpholine-N-oxide (0.288 g, 2.458 mmol). The reaction was stirred overnight and was then quenched by the addition of 10% aqueous sodium thiosulfate solution (10 mL) and ethyl acetate (15 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×15 mL). The combined organics were washed with 10% aqueous sodium thiosulfate solution (10 mL), dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 10% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 642.2 [M+H]+.

Workup

  1. customwas then quenched by the addition of 10% aqueous sodium thiosulfate solution (10 mL) and ethyl acetate (15 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate (2×15 mL)
  4. washThe combined organics were washed with 10% aqueous sodium thiosulfate solution (10 mL)
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 0 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-ca88872a00ce4818a52c2affcd498de0
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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