Water → HCID 46865573, compound

HRID 2043458Notes

Reaction equation

HRID 2043458 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[CH:12]=[C:13]([CH:18]=[C:19]([NH:21][C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)[N:20]=2)[C:14](OC)=[O:15])[CH3:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[CH:12]=[C:13]([CH2:14][OH:15])[CH:18]=[C:19]([NH:21][C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)[N:20]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 46865574HCID 46865574, compound

Product 1

HCID 46865573HCID 46865573, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

100 mg of methyl (S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinate was dissolved in 1 ml of tetrahydrofuran, 20 mg of lithium aluminum hydride was added by small portions, and the mixture was stirred at room temperature for 6 hours. The reaction solution was diluted with tetrahydrofuran, and then cooled to 0° C., and 25 μl of water, 25 μl of 2N sodium hydroxide aqueous solution, and further 75 μl of water were added, and the reaction mixture was dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 60 mg of the objective compound as pale yellow powder.

Workup

  1. temperaturecooled to 0° C.
  2. dry with materialthe reaction mixture was dried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-335c2d3bc65c4c43ba9a9d59be0d709c
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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