{1-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-4-phenyl-piperidin-4-yl}-carbamic acid tert-butyl ester → HCID 178434416, compound

HRID 2360699Notes

Reaction equation

HRID 2360699 reaction equation
C(OC(=O)[NH:7][C:8]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:39]([CH3:40])=[N:38][N:37](C4CCCCO4)[C:18]=3[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28]CC4C=CC=CC=4)=[CH:24][C:23]=3[F:36])[CH:21]=2)=[O:15])[CH2:10][CH2:9]1)(C)(C)C>CO>[NH2:7][C:8]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=3[F:36])[N:19]=[C:18]3[NH:37][N:38]=[C:39]([CH3:40])[C:17]=23)=[O:15])[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 86680320{1-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-4-phenyl-piperidin-4-yl}-carbamic acid tert-butyl ester

Product 1

HCID 178434416HCID 178434416, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
38 °C

Procedure

{1-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-4-phenyl-piperidin-4-yl}-carbamic acid tert-butyl ester (90 mg) was dissolved in methanol (2 mL) and purged with argon, then hydrogen. Palladium (10% on charcoal, 13 mg) was added and the mixture was stirred at 38° C. for 2 h. The catalyst was filtered off, the solvent was evaporated and the residue was dissolved in THF (5 mL) containing HCl (4N in dioxane, 0.14 mL). The solution was stirred at r.t. over night, the precipitate formed was filtered off. The filtrate was concentrated, the residue was re-dissolved in methanol/water (v/v=1/1, 4 mL), and concentrated hydrochloric acid (1 mL) was added. The precipitate formed was filtered off, washed with ethyl acetate and acetone and dried in air. The two filtration solids were combined yielding 45 mg (75%) of the title compound.

Workup

  1. custompurged with argon
  2. additionPalladium (10% on charcoal, 13 mg) was added
  3. filtrationThe catalyst was filtered off
  4. customthe solvent was evaporated
  5. dissolutionthe residue was dissolved in THF (5 mL)
  6. additioncontaining HCl (4N in dioxane, 0.14 mL)
  7. stirringThe solution was stirred at r.t. over night
  8. customthe precipitate formed
  9. filtrationwas filtered off
  10. concentrationThe filtrate was concentrated
  11. dissolutionthe residue was re-dissolved in methanol/water (v/v=1/1, 4 mL)
  12. additionconcentrated hydrochloric acid (1 mL) was added
  13. customThe precipitate formed
  14. filtrationwas filtered off
  15. washwashed with ethyl acetate and acetone
  16. customdried in air
  17. filtrationThe two filtration solids

Sources & evidence

ORD record
ord-e5baddcb6c9643eea89efc58818305f5
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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