Potassium Carbonate → HCID 178457523, compound

HRID 573237Notes

Reaction equation

HRID 573237 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][C:24]([NH2:28])([CH3:27])[CH2:25][NH2:26]>CN(C=O)C>[NH:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:6]2[N:7]=[C:2]([NH:26][CH2:25][C:24]([CH3:27])([NH2:28])[CH3:23])[CH:3]=[CH:4][CH:5]=2)=[N:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131282-MethylpropylenediamineHCID 178419383HCID 178419383, compound

Product 1

HCID 178457523HCID 178457523, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-(6-bromo-2-pyridyl)-1H-pyrazolo[5,4-b]pyridine (50 mg,), potassium carbonate (150.6 mg, 1.09 mmol) and 2-methylpropane-1,2-diamine (40.1 mg, 0.45 mmol) in DMF (0.7 mL) was heated at 150° C. for 24 hours. The mixture was allowed to cool, filtered and the resultant filtrate purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min] The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a white solid (33.5 mg, 36% Yield).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customthe resultant filtrate purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min] The fractions
  4. customwere collected
  5. customfreeze-dried

Sources & evidence

ORD record
ord-d060a367160747069cad2b885194970a
Source dataset
uspto-grants-2015_05
Patent number
US09029546B2

Reaction notes

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