Diisopropyl Ether → HCID 118308762, compound

HRID 923524Notes

Reaction equation

HRID 923524 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][C:8]([NH:15][C:16]([C:18]1[N:22]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH2:28][C:29]3[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=3[F:36])[C:21]2=[N:20][C:19]=1[CH3:37])=[O:17])([C:10]1[N:11]=[N:12][NH:13][N:14]=1)[CH3:9])(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[CH3:56][C:57]1([CH3:60])[CH2:59][O:58]1.C(OC(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C.O>[F:35][C:34]1[CH:33]=[CH:32][CH:31]=[C:30]([F:36])[C:29]=1[CH2:28][O:27][C:26]1[C:21]2[N:22]([C:18]([C:16]([NH:15][C:8]([C:10]3[N:14]=[N:13][N:12]([CH2:56][C:57]([OH:58])([CH3:60])[CH3:59])[N:11]=3)([CH3:9])[CH2:7][OH:6])=[O:17])=[C:19]([CH3:37])[N:20]=2)[CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 11208Isobutylene oxide3×HCID 11430Potassium Carbonate2×HCID 131734991HCID 131734991, compound

Product 1

HCID 118308762HCID 118308762, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 180 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 in 3 ml of DMF were added 100 mg of potassium carbonate and 50 μl of 2,2-dimethyloxirane, followed by stirring at 60° C. for 4 hours and then at 100° C. overnight. To the reaction mixture were added 100 mg of potassium carbonate and 50 μl of 2,2-dimethyloxirane, followed by stirring at 140° C. for 1 hour under the microwave irradiation condition. To the reaction mixture was added 50 μl of 2,2-dimethyloxirane, followed by stirring at 150° C. for 1 hour under the microwave irradiation condition. 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. 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 42 mg of 8-[(2,6-difluorobenzyl)oxy]-N-{1-hydroxy-2-[2-(2-hydroxy-2-methylpropyl)-2H-tetrazol-5-yl]propan-2-yl}-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. customat 100° C.
  2. customovernight
  3. stirringby stirring at 140° C. for 1 hour under the microwave irradiation condition
  4. stirringby stirring at 150° C. for 1 hour under the microwave irradiation condition
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  8. customthe solvent was then evaporated
  9. customThe obtained residue was purified by silica gel column chromatography
  10. customTo the obtained crude product
  11. filtrationthe insoluble materials were collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-5611c86ab07b4a489f1114aacba28601
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…