Sodium Thiosulfate → HCID 86662317, compound

HRID 1431063Notes

Reaction equation

HRID 1431063 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:12]=[CH:13][C:14]([O:17][C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])=[CH:15][CH:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 66741956HCID 66741956, compound

Product 1

HCID 86662317HCID 86662317, compoundYield 71.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-4-(5-(1-hydroxy-2-methylpropan-2-yloxy)pyridine-2-ylamino)-2-methylpyridazin-3-(2H)-one (965 mg, 2.97 mmol) was taken up in a mixture of tetrahydrofuran (25 ml) and dichloromethane (15 ml). To the suspension was added Dess-Martin Periodinane (1.64 g, 3.86 mmol) and the flask was capped and stirred for 40 minutes. An aqueous saturated solution of sodium bicarbonate (50 ml) followed by the addition of an aqueous 10% solution of sodium thiosulfate (50 ml) and the material was stirred vigorously for 15 minutes. Ethyl acetate (50 ml) was added and the contents were shaken in a separatory funnel. The organic phase was collected and washed with brine solution (50 ml). The ethyl acetate phase was collected and the aqueous phases were back extracted with dichloromethane (2×40 ml). The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo. The product was purified via trituration from hot dichloromethane/hexanes to provide a brown solid (688 mg) (M+H)+=323 m/e.

Workup

  1. customthe flask was capped
  2. stirringthe material was stirred vigorously for 15 minutes
  3. stirringthe contents were shaken in a separatory funnel
  4. customThe organic phase was collected
  5. washwashed with brine solution (50 ml)
  6. customThe ethyl acetate phase was collected
  7. extractionthe aqueous phases were back extracted with dichloromethane (2×40 ml)
  8. dry with materialThe combined organic phases were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe product was purified via trituration from hot dichloromethane/hexanes

Sources & evidence

ORD record
ord-1fc59838c0e941c7a2944a58ca596983
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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