Hydrogen Bromide → HCID 58452506, compound

HRID 70605Notes

Reaction equation

HRID 70605 reaction equation
Br.[CH:2]1([C:5]2[CH:6]=[CH:7][C:8](/[C:13](/[C:21]3[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=3)=[CH:14]/[CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])=[N:9][C:10]=2[O:11]C)[CH2:4][CH2:3]1.O>O1CCOCC1>[CH:2]1([C:5]2[C:10](=[O:11])[NH:9][C:8](/[C:13](/[C:21]3[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=3)=[CH:14]/[CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])=[CH:7][CH:6]=2)[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 67399046HCID 67399046, compound

Product 1

HCID 58452506HCID 58452506, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

48% hydrobromic acid (2 mL) was added to a solution of N-{(3E)-4-(5-cyclopropyl-6-methoxypyridin-2-yl)-4-[4-(methylsulfanyl)phenyl]but-3-en-1-yl}acetamide (87 mg) in 1,4-dioxane (2 mL), and the mixture was stirred at 80° C. for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was recrystallized from a mixed solvent of chloroform-ethyl acetate-hexane. Filtration gave the title compound as a colorless solid (54 mg, 64%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was recrystallized from a mixed solvent of chloroform-ethyl acetate-hexane
  7. filtrationFiltration

Sources & evidence

ORD record
ord-88f21b34cd7649b1ad54b684ef066bee
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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