Hydrochloric Acid → HCID 71247646, compound

HRID 1055095Notes

Reaction equation

HRID 1055095 reaction equation
[F:1][C:2]1[C:3]([NH:28][CH:29]([C:35]2([CH3:39])[CH2:38][CH2:37][CH2:36]2)[CH2:30][C:31]([O:33][CH3:34])=[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(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)=[N:6][CH:7]=1.Cl>C(#N)C>[F:1][C:2]1[C:3]([NH:28][CH:29]([C:35]2([CH3:39])[CH2:36][CH2:37][CH2:38]2)[CH2:30][C:31]([O:33][CH3:34])=[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)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71247788HCID 71247788, compound2×

Product 1

HCID 71247646HCID 71247646, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a racemic solution of methyl 3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-3-(1-methylcyclobutyl)propanoate, 119a, (3.3 g, 5.9 mmol) in acetonitrile (25 mL) was added HCl (26 mL of 4N solution in dioxane). The reaction mixture was heated to 65° C. for 4 hours. The solution was cooled to room temperature and the solvents were removed under reduced pressure. The mixture was flushed with acetonitrile after which aqueous sodium bicarbonate and ethyl acetate were added. The phases were separated and the aqueous layer washed with ethyl acetate. The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (EtOAc/Hexanes) to afford the desired product: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.34 minutes (M+H) 403.11.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthe solvents were removed under reduced pressure
  3. customThe mixture was flushed with acetonitrile after which aqueous sodium bicarbonate and ethyl acetate
  4. additionwere added
  5. customThe phases were separated
  6. washthe aqueous layer washed with ethyl acetate
  7. dry with materialThe combined organic phases were dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified via silica gel chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6b5c50fadb0c4df4b1f97fa6e7c5d82f
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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