Hydrochloric Acid → HCID 71247355, compound

HRID 2171869Notes

Reaction equation

HRID 2171869 reaction equation
[F:1][C:2]1[C:3]([NH:28][CH:29]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:30][C:31](OC)=[O:32])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)=[N:6][CH:7]=1.[BH4-].[Li+].Cl>C1COCC1.CO.ClCCl>[F:1][C:2]1[C:3]([NH:28][CH:29]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:30][CH2:31][OH:32])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:19])=[O:20])[CH:9]=2)=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 71247857HCID 71247857, compound

Product 1

HCID 71247355HCID 71247355, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of racemic methyl 3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-4,4-dimethylpentanoate (4.00 g, 7.36 mmol) in THF (160 mL) and MeOH (10 mL) was added lithium borohydride (29.44 mL of 2 M solution, 58.87 mmol) dropwise over 30 minutes. The reaction mixture was slowly warmed to room temperature and then re-cooled to 0° C. A 1N HCl solution (294 mL, 294 mmol) was added dropwise. The mixture was stirred for 15 minutes and then diluted with dichloromethane. The phases were separated and the aqueous phase was extracted again with dichloromethane. The combined organic phases were washed with aqueous saturated NaHCO3 solution and brine, dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (EtOAc/Hexanes) to afford 3.79 g of the desired product.

Workup

  1. temperaturere-cooled to 0° C
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted again with dichloromethane
  4. washThe combined organic phases were washed with aqueous saturated NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified via silica gel chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-56ec9445ce0d4efa8c82d92352960d29
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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