Water → HCID 118308700, compound

HRID 923485Notes

Reaction equation

HRID 923485 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][C:8]([NH:12][C:13]([C:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[C:23]([O:24][CH2:25][C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])[C:18]2=[N:17][C:16]=1[CH3:34])=[O:14])([C:10]#[N:11])[CH3:9])(C)(C)C.[N-:47]=[N+:48]=[N-:49].[Na+].[Cl-].[NH4+].O>CN(C=O)C.C(OCC)(=O)C>[F:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:26]=1[CH2:25][O:24][C:23]1[C:18]2[N:19]([C:15]([C:13]([NH:12][C:8]([C:10]3[N:11]=[N:47][NH:48][N:49]=3)([CH3:9])[CH2:7][OH:6])=[O:14])=[C:16]([CH3:34])[N:17]=2)[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 131734988HCID 131734988, compound

Product 1

HCID 118308700HCID 118308700, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 60 mg of N-(1-{[tert-butyl (diphenyl)silyl]oxy}-2-cyanopropan-2-yl)-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 2 ml of DMF were added 70 mg of sodium azide and 60 mg of ammonium chloride, followed by stirring at 120° C. for 4 hours. The reaction mixture was left to be cooled to room temperature and water was then added thereto, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium 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 was added ethyl acetate, and the insoluble materials were collected by filtration and dried under reduced pressure to obtain 19 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.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was then evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography
  8. customTo the obtained crude product
  9. filtrationthe insoluble materials were collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-694deba6d4a5468f965d5da73ab86b13
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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