Ethanol → HCID 58049365, compound

HRID 467967Notes

Reaction equation

HRID 467967 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([C:16]([C:18]2[N:22]=[CH:21][N:20]([CH3:23])[N:19]=2)=[O:17])[CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30](OC)=[O:31])[CH:25]=1.C(O)C.[BH4-].[Na+]>O.CC(C)=O>[F:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][OH:31])[CH:25]=2)=[CH:4][C:5]([CH2:8][N:9]([CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[C:16]([C:18]2[N:22]=[CH:21][N:20]([CH3:23])[N:19]=2)=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 58049388HCID 58049388, compound

Product 1

HCID 58049365HCID 58049365, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A mixture of methyl 2′-fluoro-5′-([[(1-methyl-1H-1,2,4-triazol-3-yl)carbonyl](tetrahydro-2H-pyran-4-yl)amino]methyl)biphenyl-3-carboxylate (318 mg), ethanol (14 mL) and sodium borohydride (532 mg) was heated under reflux for 16 hours. After leaving the mixture to cool, water-acetone was added and extraction was conducted with chloroform. The organic layer was dried over anhydrous sodium sulfate. After filtering off the desiccant, the solvents were distilled off under reduced pressure and the resulting residue was purified by column chromatography (silica gel cartridge; methanol/chloroform=1:99 to 3:97) to give the titled compound (17 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customAfter leaving the mixture
  4. temperatureto cool
  5. extractionextraction
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationAfter filtering off the desiccant
  8. distillationthe solvents were distilled off under reduced pressure
  9. customthe resulting residue was purified by column chromatography (silica gel cartridge; methanol/chloroform=1:99 to 3:97)

Sources & evidence

ORD record
ord-3e0caef293f649b68f6cac42ca38d401
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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