HCID 136402335, compound → HCID 136140503, compound

HRID 1594394Notes

Reaction equation

HRID 1594394 reaction equation
Cl.[CH:2]1([C:6]2[NH:7][N:8]=[C:9]3[C:14]=2[CH:13]=[CH:12][C:11](=[O:15])[NH:10]3)[CH2:5][CH2:4][CH2:3]1>CO.[Pd]>[CH:2]1([C:6]2[NH:7][N:8]=[C:9]3[C:14]=2[CH2:13][CH2:12][C:11](=[O:15])[NH:10]3)[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 136402335HCID 136402335, compound

Product 1

HCID 136140503HCID 136140503, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To an aliquot of 3-cyclobutyl-2,7-dihydro-pyrazolo[3,4-b]pyridin-6-one-hydrochloride salt (0.20 mg, 0.87 mmol) in MeOH (30 mL) was added 10% Pd/C (200 mg). The reaction mixture, in a hydrogenation bottle, was pressured with 45 psi H2, and then the reaction mixture was heated to 65° C. (internal). After 14 hr, the reaction was cooled to room temperature, filtered through a plug of diatomaceous earth, and concentrated under reduced pressure. Partial purification of this material was accomplished by MPLC using a 10 g ISCO column, eluting with 2% MeOH/CH2Cl2 with 0.2% NH4OH. The product-containing fractions with biproduct were collected and concentrated. This material was further purified by trituration with Et2O. The product was filtered off and dried under reduced pressure to afford the title compound (40.0 mg, 23% yield) as a colorless solid. Rf=0.54 (10% MeOH/CH2Cl2). 400 MHz 1H NMR (CD3OD) d 3.54 (dddd, J=8.8, 8.7, 8.7, 8.7 Hz, 1H), 2.75 (apt t, J=7.5 Hz, 2H), 2.58 (apt t, J=7.5 Hz, 2H), 2.33-2.23 (m, 4H), 2.07 (dddd, J=18.7, 9.5, 9.5, 9.5 Hz, 1H), 7.75-7.48 (m, 1H). LRMS m/z (APCI+) 192 (M+1).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. filtrationfiltered through a plug of diatomaceous earth
  3. concentrationconcentrated under reduced pressure
  4. customPartial purification of this material
  5. washeluting with 2% MeOH/CH2Cl2 with 0.2% NH4OH
  6. customThe product-containing fractions with biproduct were collected
  7. concentrationconcentrated
  8. customThis material was further purified by trituration with Et2O
  9. filtrationThe product was filtered off
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-0d7ffa95f6c44923ad60d12415673764
Source dataset
uspto-grants-2007_11
Patent number
US07300944B2

Reaction notes

Loading…