Hydrogen Bromide → HCID 136055524, compound

HRID 2101044

Reaction equation

HRID 2101044 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19]C)=[CH:16][CH:17]=2)[CH:12]=[C:11]([NH:21][C:22]2[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=2)[N:10]=1.Br>C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[CH:12]=[C:11]([NH:21][C:22]2[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=2)[N:10]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 23633788[1-(2,4-difluoro-phenyl)-6-methoxy-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine

Product 1

HCID 136055524HCID 136055524, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of [1-(2,4-difluoro-phenyl)-6-methoxy-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine (11.0 g) in 10 mL acetic acid was added hydrobromic acid (1 mL, 40%). The mixture was heated at 180° C. for 30 min under microwave irradiation. After cooling, most of the solvent was removed under reduced pressure, the residue was dissolved in 100 mL of ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried with anhydrous sodium sulfate and concentrated to give an oil (0.92 g), which was used for the next reaction without further purification. (LC-MS m/e 353 MH+).

Workup

  1. temperatureAfter cooling, most of the solvent
  2. customwas removed under reduced pressure
  3. dissolutionthe residue was dissolved in 100 mL of ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-651daadcade84d478828c1227c5f054e
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Linked notes

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