Potassium Carbonate → HCID 57964993, compound

HRID 1931684Notes

Reaction equation

HRID 1931684 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:2]1=2.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[C:28]3=[N:29][CH:30]=[N:31][C:32](Cl)=[C:27]3[CH:26]=[N:25]2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([N:24]2[C:28]3=[N:29][CH:30]=[N:31][C:32]([O:10][C:7]4[CH:8]=[CH:9][C:2]5[S:1][CH:5]=[CH:4][C:3]=5[CH:6]=4)=[C:27]3[CH:26]=[N:25]2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 12203499Benzo[b]thiophen-5-olHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57964993HCID 57964993, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of benzo[b]thiophen-5-ol (MCAT GmbH, Konstanz, Germany; 300 mg, 2 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 607 mg, 1.8 mmol), and potassium carbonate (414 mg, 3 mmol) in dimethylformamide (20 mL) was heated at 80° C. for 3 h. The mixture was cooled and then poured into saturated aqueous ammonium chloride solution, and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried (magnesium sulfate), filtered, evaporated and chromatographed, eluting with 50% ethyl acetate/hexanes to give 4-[4-(benzo[b]thio-phen-5-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester as a pale yellow foam.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe resulting mixture was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed
  8. washeluting with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d504190eabce4cb785f61f494704f91f
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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