Potassium Sodium Tartrate → HCID 118308736, compound

HRID 923519Notes

Reaction equation

HRID 923519 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[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[CH:32]=[CH:31][C:26]([C:27](OC)=[O:28])=[CH:25][CH:24]=3)([CH3:22])[CH2:20][OH:21])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[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[CH:24]=[CH:25][C:26]([CH2:27][OH:28])=[CH:31][CH:32]=3)([CH3:22])[CH2:20][OH:21])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 86583787Diisobutylaluminumhydride toluene2×HCID 118308699HCID 118308699, compound

Product 1

HCID 118308736HCID 118308736, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 35 mg of methyl 4-{2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-1-hydroxypropan-2-yl}benzoate in 1.4 ml of THF were added dropwise 0.17 ml of a 1 M diisobutylaluminum hydride/toluene solution at −78° C., followed by stirring at 0° C. for 3 hours. To the reaction mixture was added 0.14 ml of a 1 M diisobutylaluminum hydride/toluene solution at 0° C., followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous Rochelle salt solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated. The residue was purified by silica gel column chromatography to obtain 20 mg of 8-[(2,6-difluorobenzyl)oxy]-N-{1-hydroxy-2-[4-(hydroxymethyl)phenyl]propan-2-yl}-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. stirringby stirring for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was then evaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-73c3096c7de444048fcabdf8ee66cf3d
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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