Water → HCID 76283193, compound

HRID 923517Notes

Reaction equation

HRID 923517 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C:19]([C:26]3[S:30][C:29]([CH3:31])=[N:28][CH:27]=3)([CH3:25])[C:20](OCC)=[O:21])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[BH4-].[Na+].O>C(O)C.O1CCCC1>[F:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C:19]([C:26]3[S:30][C:29]([CH3:31])=[N:28][CH:27]=3)([CH3:25])[CH2:20][OH:21])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 118308715HCID 118308715, compound

Product 1

HCID 76283193HCID 76283193, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 110 mg of ethyl 2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-(2-methyl-1,3-thiazol-5-yl)propanoate in 3.3 ml of ethanol and 0.66 ml of tetrahydrofuran were added 40 mg of sodium borohydride at 0° C., followed by stirring at room temperature for 16 hours. To the reaction mixture was added water, followed by extraction with chloroform. The organic layer was 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 obtain 80 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[1-hydroxy-2-(2-methyl-1,3-thiazol-5-yl)propan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was then evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-db2bc01258dd4d2ebc5a2057b9ccb777
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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