HCID 69419183, compound → HCID 69417374, compound

HRID 1296353Notes

Reaction equation

HRID 1296353 reaction equation
[CH2:1]([N:8]([CH2:32][CH2:33][OH:34])[CH2:9][CH:10]([C:12]1[C:16]([CH3:17])=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[N:13]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([N:8]1[CH2:32][CH2:33][O:34][CH:10]([C:12]2[C:16]([CH3:17])=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[N:14]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[N:13]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 69419183HCID 69419183, compound

Product 1

HCID 69417374HCID 69417374, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

The suspension of 2-[benzyl-(2-hydroxy-ethyl)-amino]-1-[5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-methyl-1H-pyrazol-3-yl]-ethanol 2A-3 (150 mg, 0.3 mmol) in 48% hydrobromic acid (0.3 ml) was heated to 100° C. for 2 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and partitioned with ethyl acetate and saturated NaHCO3. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (silica gel, 40% ethyl acetate/hexanes) to give the title compound 5A-1 (77 mg).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. custompartitioned with ethyl acetate and saturated NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (silica gel, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9413cab5012d43a5950b44de62a634e6
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

Loading…