Potassium Carbonate → HCID 178420747, compound

HRID 1046570Notes

Reaction equation

HRID 1046570 reaction equation
CS([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[N:5]=1)=O.[N:19]1(C(OC(C)(C)C)=O)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.CCOC(C)=O>[N:19]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[NH:12][N:11]=3)[N:5]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 178504609HCID 178504609, compound

Product 1

HCID 178420747HCID 178420747, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 3-(4-methylsulfinylpyrimidin-2-yl)-1H-pyrazolo[5,4-b]pyridine (45 mg, 0.17 mmol), tert-butyl piperazine-1-carboxylate (100 mg, 0.53 mmol) and potassium carbonate (100 mg, 0.72 mmol) in NMP (0.5 ml) were stirred at 125° C. for 60 minutes in the microwave. The reaction mixture was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate and brine. After drying over MgSO4 and concentration the residue was taken up in DCM (2 ml) and treated with TFA (1 ml). The reaction was allowed to stir at RT for 3 hours and concentrated in vacuo. and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A 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 pink solid (10 mg, 11% Yield).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialAfter drying over MgSO4 and concentration the residue
  3. additiontreated with TFA (1 ml)
  4. stirringto stir at RT for 3 hours
  5. concentrationconcentrated in vacuo
  6. customand the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  7. customThe fractions were collected
  8. customfreeze-dried

Sources & evidence

ORD record
ord-75e5083d27854428ba8cfd99469ca1bf
Source dataset
uspto-grants-2013_10
Patent number
US08569337B2

Reaction notes

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