Methyl iodide → HCID 118308718, compound

HRID 923522Notes

Reaction equation

HRID 923522 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C:19]([C:23]3[N:24]=[N:25][NH:26][N:27]=3)([CH3:22])[CH2:20][OH:21])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[C:33](=O)([O-])[O-].[K+].[K+].CI.C(OC(C)C)(C)C>CN(C=O)C.C(O)(C)C.O>[F:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C:19]([C:23]3[N:27]=[N:26][N:25]([CH3:33])[N:24]=3)([CH3:22])[CH2:20][OH:21])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 118308700HCID 118308700, compound

Product 1

HCID 118308718HCID 118308718, compoundYield 28.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 245 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[1-hydroxy-2-(2H-tetrazol-5-yl)propan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 5 ml of DMF were added 200 mg of potassium carbonate and 50 μl of methyl iodide, followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography. To the obtained crude product were added isopropyl alcohol and diisopropyl ether, and the insoluble materials were collected by filtration and dried under reduced pressure to obtain 73 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[1-hydroxy-2-(2-methyl-2H-tetrazol-5-yl)propan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide (Ex7a). Further, to the other crude product was added diisopropyl ether, and the insoluble materials were collected by filtration and dried under reduced pressure to obtain 27 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[1-hydroxy-2-(1-methyl-1H-tetrazol-5-yl)propan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide (Ex7b).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography
  6. customTo the obtained crude product
  7. filtrationthe insoluble materials were collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e2b5f2b4cb4c4dc2a378d3f755836614
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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