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Hydrogen Bromide → HCID 58452756, compound

HRID 70648
Notes
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Reaction equation

HRID 70648 reaction equation
Br.[NH2:2][C:3]1[CH:4]=[CH:5][C:6](/[C:11](/[C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[CH:12]/[C@@H:13]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]2)=[N:7][C:8]=1[O:9]C.O>O1CCOCC1>[NH2:2][C:3]1[C:8](=[O:9])[NH:7][C:6](/[C:11](/[C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH3:27])([CH3:26])[CH3:28])=[CH:23][CH:24]=2)=[CH:12]/[C@H:13]2[CH2:14][CH2:15][C:16](=[O:18])[NH:17]2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 67399550HCID 67399550, compound

Product 1

HCID 58452756HCID 58452756, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

48% hydrobromic acid (0.5 mL) was added to a solution of (5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one (20 mg) in 1,4-dioxane (1 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. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1) and crystallized from chloroform-ethyl acetate to give the title compound as a light brown powder (8 mg, 44%).

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. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1)
  6. customcrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-87d8b283ec21442a9b8bd1ccb7a69448
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes