6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-phenyl-piperidin-4-yl)-amide → HCID 178434418, compound

HRID 2360701Notes

Reaction equation

HRID 2360701 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([NH:20][C:21]([C:23]2[C:24]3[C:46]([CH3:47])=[N:45][N:44](C4CCCCO4)[C:25]=3[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([O:35]CC4C=CC=CC=4)=[CH:31][C:30]=3[F:43])[CH:28]=2)=[O:22])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO>[C:14]1([C:11]2([NH:20][C:21]([C:23]3[C:24]4[C:46]([CH3:47])=[N:45][NH:44][C:25]=4[N:26]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=4[F:43])[CH:28]=3)=[O:22])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 866803236-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-phenyl-piperidin-4-yl)-amide

Product 1

HCID 178434418HCID 178434418, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-phenyl-piperidin-4-yl)-amide (275 mg) was dissolved in methanol (10 mL) and purged with argon, then hydrogen. Palladium (10% on charcoal, 82 mg) was added and the mixture was stirred at 40° C. for 2 h, then at r.t. over night. The catalyst was filtered off, the solvent was evaporated and the residue was dissolved in methanol (4 mL) and water (1 ml). Concentrated aqueous hydrochloric acid (1 mL) was added and the solution was stirred for 3 d. The solution was kept at −20° C. in a freezer until a precipitate appeared, which was filtered off and washed with methanol giving 6-(2-Fluoro-4-hydroxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-phenyl-piperidin-4-yl)-amide (144 mg). A second fraction of title compound was obtained by storing the filtrate at −20° C. for a day and filtering off the precipitated product (31 mg, 95% overall yield).

Workup

  1. custompurged with argon
  2. additionPalladium (10% on charcoal, 82 mg) was added
  3. waitat r.t. over night
  4. filtrationThe catalyst was filtered off
  5. customthe solvent was evaporated
  6. dissolutionthe residue was dissolved in methanol (4 mL)
  7. additionConcentrated aqueous hydrochloric acid (1 mL) was added
  8. stirringthe solution was stirred for 3 d
  9. customwas kept at −20° C. in a freezer until a precipitate
  10. filtrationwhich was filtered off
  11. washwashed with methanol

Sources & evidence

ORD record
ord-f04960885f354db5a3518764911ae978
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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