Hydrogen Bromide → HCID 67069927, compound

HRID 2390814Notes

Reaction equation

HRID 2390814 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[C:9]([O:14]C)=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][C:5]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:4][C:3]=1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:23]=1.Br.C([O-])(O)=O.[Na+]>CC(O)=O>[NH2:1][C:2]1[C:7]([C:8]2[C:9](=[O:14])[NH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][C:5]([C:16]([CH3:17])([CH3:18])[CH3:19])=[CH:4][C:3]=1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 67070018HCID 67070018, compound

Product 1

HCID 67069927HCID 67069927, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

step 5—A mixture of 86 (0.050 g, 0.11 mmol), 48% HBr (0.050 mL) and AcOH (2 mL) in a sealed tube was heated overnight at 70° C. The reaction mixture was cooled to RT, carefully poured into a cold saturated aqueous NaHCO3 and then extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and concentrated. The crude residue was purified by SiO2 chromatography and eluted with 10% MeOH/DCM to afford 32 mg (66%) of N-(4-{2-[2-amino-5-tert-butyl-3-(2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-ethyl}-phenyl)-methanesulfonamide (88) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluted with 10% MeOH/DCM

Sources & evidence

ORD record
ord-b3afb77292c442f98a58dc95d92e9cc1
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…