Diisopropyl Ether → HCID 118308761, compound

HRID 923521Notes

Reaction equation

HRID 923521 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:12][CH2:13][C:14]([NH:21][C:22]([C:24]1[N:28]2[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH2:34][C:35]3[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=3[F:42])[C:27]2=[N:26][C:25]=1[CH3:43])=[O:23])([C:16]1[N:17]=[N:18][NH:19][N:20]=1)[CH3:15])(C)(C)C.Cl[C:57]([F:62])([F:61])C([O-])=O.[Na+].C(OC(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C.O>[F:41][C:40]1[CH:39]=[CH:38][CH:37]=[C:36]([F:42])[C:35]=1[CH2:34][O:33][C:32]1[C:27]2[N:28]([C:24]([C:22]([NH:21][C:14]([C:16]3[N:17]=[N:18][N:19]([CH:57]([F:62])[F:61])[N:20]=3)([CH3:15])[CH2:13][OH:12])=[O:23])=[C:25]([CH3:43])[N:26]=2)[CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 131734991HCID 131734991, compound

Product 1

HCID 118308761HCID 118308761, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 153 mg of potassium carbonate and 5 ml of DMF was added dropwise a solution of 346 mg of N-[1-{[tert-butyl (diphenyl)silyl]oxy}-2-(2H-tetrazol-5-yl)propan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide and 158 mg of sodium chloro(difluoro)acetate in 3 ml of DMF at an inner temperature of 95° C., followed by stirring at the same temperature for 1 hour. After leaving to be cooled to room temperature, water was added thereto, 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 ethyl acetate and diisopropyl ether, and the insoluble materials were collected by filtration and dried under reduced pressure to obtain 98 mg of 8-[(2,6-difluorobenzyl)oxy]-N-{2-[2-(difluoromethyl)-2H-tetrazol-5-yl]-1-hydroxypropan-2-yl}-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

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

Sources & evidence

ORD record
ord-9f52e547d2fb43d6b43b5b7bf4eefc9f
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…