Acetone → 3-[(3,4-Dihydroxy-4-methylpentyl)oxy]-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamide

HRID 2167225Notes

Reaction equation

HRID 2167225 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[N:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:11]=1[C:12]([NH2:14])=[O:13].[OH2:26].CC(C)=[O:29]>[Os](=O)(=O)(=O)=O>[OH:26][CH:22]([C:23]([OH:29])([CH3:25])[CH3:24])[CH2:21][CH2:20][O:19][C:15]1[CH:16]=[N:17][CH:18]=[C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])[C:11]=1[C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 569706863-[(2-Fluoro-4-iodophenyl)amino]-5-[(4-methylpent-3-en-1-yl)oxy]isonicotinamide

Product 1

HCID 569706873-[(3,4-Dihydroxy-4-methylpentyl)oxy]-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamide

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

252 mg of 3-[(2-fluoro-4-iodophenyl)amino]-5-[(4-methylpent-3-en-1-yl)oxy]isonicotinamide (0.554 mmol, 1 eq.) were dissolved in 36 ml of Acetone and 6 ml of water were added to form a suspension. Then 454 mg of N-methyl-morpholino-N-oxide 3.875, 7 eq.) and 555 μl of an osmiumtetroxide solution (2.5 weight % in tert.-butanol, 0.044 mmol, 0.08 eq.) were added and the formed suspension was stirred for 18 hours at room temperature. The reaction mixture was concentrated in vacuo and the residue was partitioned between 50 ml each of water and dichloromethane/isopropanole (4:1). The aqueouse layer was separated and reextracted twice with dichloromethane/isopropanole (4:1). The combined organic layers were washed with brine, dried over a silicone filter and concentrated to afford 272 mg (0.55 mmol, 100%) of the analytically pure target compound which required no further purification.

Workup

  1. customto form a suspension
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between 50 ml each of water and dichloromethane/isopropanole (4:1)
  4. customThe aqueouse layer was separated
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over a silicone
  7. filtrationfilter
  8. concentrationconcentrated
  9. customto afford 272 mg (0.55 mmol, 100%) of the analytically pure target compound which
  10. customno further purification

Sources & evidence

ORD record
ord-1aa614105b0544bc9347d56139722aa7
Source dataset
uspto-grants-2015_06
Patent number
US09045429B2

Reaction notes

Loading…