Hydrogen Bromide → HCID 136055522, compound

HRID 2101041Notes

Reaction equation

HRID 2101041 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:8][C:7]([NH:19][C:20]1[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=1)=[CH:6]2.Br>C(O)(=O)C>[CH3:25][C:23]1[NH:22][N:21]=[C:20]([NH:19][C:7]2[N:8]=[C:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10]3[C:5]([CH:6]=2)=[CH:4][C:3]([OH:2])=[CH:12][CH:11]=3)[CH:24]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 23634011HCID 23634011, compound

Product 1

HCID 136055522HCID 136055522, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
180 °C

Procedure

The mixture of (6-methoxy-1-phenyl-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (100 mg), 40% aq. HBr (1 ml), acetic acid (2 ml) was heated at 180° C. for 30 minutes under microwave irradiation. After reaction finished, the mixture was evaporated to oil by reduced pressure and was dissolved in 50 ml ethyl acetate. The organic layer was washed with aq. NaHCO3 and evaporated to give 70 mg of crude 3-(5-methyl-1H-pyrazol-3-ylamino)-1-phenyl-isoquinolin-6-ol. LC-MS m/e 317(MH+).

Workup

  1. customAfter reaction
  2. customthe mixture was evaporated to oil by reduced pressure
  3. dissolutionwas dissolved in 50 ml ethyl acetate
  4. washThe organic layer was washed with aq. NaHCO3
  5. customevaporated

Sources & evidence

ORD record
ord-5e13cb1263bc44238db9e5ef5ec7ac76
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

Loading…