Ethyl Acetate → HCID 76283194, compound

HRID 923523Notes

Reaction equation

HRID 923523 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][C:8]([NH:17][C:18]([C:20]1[N:24]2[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH2:30][C:31]3[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=3[F:38])[C:23]2=[N:22][C:21]=1[CH3:39])=[O:19])([C:10]1[N:11]=[N:12][N:13]([CH2:15][CH3:16])[N:14]=1)[CH3:9])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C(OCC)(=O)C>C1COCC1>[F:37][C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([F:38])[C:31]=1[CH2:30][O:29][C:28]1[C:23]2[N:24]([C:20]([C:18]([NH:17][C:8]([C:10]3[N:11]=[N:12][N:13]([CH2:15][CH3:16])[N:14]=3)([CH3:9])[CH2:7][OH:6])=[O:19])=[C:21]([CH3:39])[N:22]=2)[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11078149TBAF tetrahydrofuranHCID 131734995HCID 131734995, compound

Product 1

HCID 76283194HCID 76283194, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 137 mg of N-[1-{[tert-butyl (diphenyl)silyl]oxy}-2-(2-ethyl-2H-tetrazol-5-yl)propan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 3 ml of THF was added 0.3 ml of a 1 M tetrabutylammonium fluoride/THF solution, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and 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, washed with diisopropyl ether, and dried under reduced pressure to obtain 75 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[2-(2-ethyl-2H-tetrazol-5-yl)-1-hydroxypropan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography
  3. customTo the obtained crude product
  4. filtrationthe insoluble materials were collected by filtration
  5. washwashed with diisopropyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5649448aed744bc1879b9fded0e46b28
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…