Hydrogen Bromide → HCID 58452833, compound

HRID 70636Notes

Reaction equation

Br.[C:2]([C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([O:28]C)[N:22]=2)=[CH:13]\[C@@H:14]2[N:18]([CH3:19])[C:17](=[O:20])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].O>O1CCOCC1>[C:2]([C:6]1[CH:7]=[CH:8][C:9](/[C:12](/[C:21]2[NH:22][C:23](=[O:28])[C:24]([Cl:27])=[CH:25][CH:26]=2)=[CH:13]\[C@H:14]2[CH2:15][CH2:16][C:17](=[O:20])[N:18]2[CH3:19])=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 65 °C

Procedure

48% hydrobromic acid (3 mL) was added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]-1-methylpyrrolidin-2-one (152 mg) in 1,4-dioxane (6 mL), and the mixture was stirred at 65° C. for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0→98:2) to give a colorless powder (151 mg). This was recrystallized from ethyl acetate-hexane to give the title compound as a colorless powder (99 mg).

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0→98:2)

Sources & evidence

ORD record: ord-5e011a771d4c4546a04a3b8f22f7daa0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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