Hydrogen Bromide → HCID 67396402, compound

HRID 70645Notes

Reaction equation

HRID 70645 reaction equation
Br.[CH:2]1([O:7][C:8]2[CH:9]=[CH:10][C:11](/[C:16](/[C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=3)=[CH:17]/[C@@H:18]3[N:22](CC4C=CC(OC)=CC=4OC)[C:21](=[O:34])[CH2:20][CH2:19]3)=[N:12][C:13]=2[O:14]C)[CH2:6][CH2:5][CH2:4][CH2:3]1.O>O1CCOCC1>[CH:2]1([O:7][C:8]2[C:13](=[O:14])[NH:12][C:11](/[C:16](/[C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:37][CH:36]=3)=[CH:17]/[C@H:18]3[CH2:19][CH2:20][C:21](=[O:34])[NH:22]3)=[CH:10][CH:9]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 67398518HCID 67398518, compound

Product 1

HCID 67396402HCID 67396402, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

48% hydrobromic acid (3 mL) was added to a solution of (5R)-5-{(E)-2-[5-(cyclopentyloxy)-6-methoxypyridin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (184 mg) in 1,4-dioxane (2 mL), and the mixture was stirred at 65° C. for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. A solution of the residue in trifluoroacetic acid (4 mL) and anisole (2 mL) was stirred at 80° C. for six hours. The solvent was evaporated from the reaction solution under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1→4:1) and powdered with ethyl acetate-diethyl ether-hexane to give the title compound as a colorless amorphous (59 mg, 47%).

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. customafter which the solvent was evaporated under reduced pressure
  5. stirringA solution of the residue in trifluoroacetic acid (4 mL) and anisole (2 mL) was stirred at 80° C. for six hours
  6. customThe solvent was evaporated from the reaction solution under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:1→4:1)

Sources & evidence

ORD record
ord-a8a715117a644f8e96ea9a4f0dbce47f
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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