Sodium periodate → HCID 118081840, compound

HRID 2279272Notes

Reaction equation

HRID 2279272 reaction equation
OC[C:3]1([OH:25])[C:8]2=[N:9][C:10]([C:13]3[S:17][C:16]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)=[N:15][C:14]=3[CH3:24])=[CH:11][CH:12]=[C:7]2[O:6][CH2:5][CH2:4]1.I([O-])(=O)(=O)=O.[Na+]>O1CCOCC1.O.ClCCl>[CH3:24][C:14]1[N:15]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:17][C:13]=1[C:10]1[N:9]=[C:8]2[C:3](=[O:25])[CH2:4][CH2:5][O:6][C:7]2=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 131733482HCID 131733482, compound

Product 1

HCID 118081840HCID 118081840, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The crude 4-(hydroxymethyl)-6-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-2,3-dihydropyrano[3,2-b]pyridin-4-ol from step e was dissolved in a 1:1 mixture of dioxane (40 mL) and H2O (40 mL), and sodium periodate (2.22 g, 10.76 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with dichloromethane (50 mL) and H2O (50 mL) and the two layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography (CH2Cl2/MeOH=100/1) to afford the title compound as a yellow solid (1.7 g, two-step yield: 48%). 1H NMR (400 Mz, CDCl3): 2.76 (s, 3H); 3.02 (t, J=6.6, 2H); 4.66 (t, J=6.9, 2H); 7.49 (d, J=9, 1 H); 7.62-7.58 (m, 1H); 7.75 (d, J=8.7, 1 H); 8.45 (d, J=7.8, 1 H); 8.71 (d, J=3.9, 1H); 9.28 (s, 1H).

Workup

  1. additionwas added
  2. customthe two layers were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography (CH2Cl2/MeOH=100/1)

Sources & evidence

ORD record
ord-a233e98e340547aab672928195ccd7ad
Source dataset
uspto-grants-2015_09
Patent number
US09133218B2

Reaction notes

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