2,6-Lutidine → HCID 57458190, compound

HRID 1020217Notes

Reaction equation

HRID 1020217 reaction equation
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[C:16]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=3[F:25])=[C:15]([CH3:26])[C:14](=[O:27])[N:13]([CH3:28])[CH:12]=2)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=C.I([O-])(=O)(=O)=[O:30].[Na+].N1C(C)=CC=CC=1C>O1CCOCC1.O.C(Cl)Cl.[Os](=O)(=O)(=O)=O>[F:25][C:19]1[CH:20]=[C:21]([I:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:16]1[C:11]([NH:10][S:7]([C:4]2([CH2:1][CH:2]=[O:30])[CH2:5][CH2:6]2)(=[O:9])=[O:8])=[CH:12][N:13]([CH3:28])[C:14](=[O:27])[C:15]=1[CH3:26]

Participants

8

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 58990847HCID 58990847, compound

Product 1

HCID 57458190HCID 57458190, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-allyl-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropane-1-sulfonamide (98 mg, 0.19 mmol) in a mixture of dioxane (3 mL) and H2O (1 mL) is added sodium periodate (158 mg, 0.74 mmol), 2,6-lutidine (0.043 mL, 0.37 mmol) and osmium tetraoxide (0.060 mL, 4% in H2O, 0.0093 mmol) The reaction mixture is stirred at room temperature for 4 h. The solution is diluted with CH2Cl2 (20 mL), washed with aqueous HCl (20 mL, 2N), dried over MgSO4 and concentrated to give N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1-(2-oxoethyl)cyclopropane-1-sulfonamide, which is used for the next step without any purification.

Workup

  1. washwashed with aqueous HCl (20 mL, 2N)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-928a133e83b0466581ca90d27170ac8f
Source dataset
uspto-grants-2014_05
Patent number
US08716318B2

Reaction notes

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