HCID 136623188, compound → HCID 178434391, compound

HRID 2279111Notes

Reaction equation

HRID 2279111 reaction equation
C([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([CH2:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:19]=[C:18]3[N:29](C4CCCCO4)[N:30]=[C:31]([CH3:32])[C:17]=23)[C@@H:10]([CH3:39])[CH2:9]1)C1C=CC=CC=1>CO>[CH3:39][C@H:10]1[CH2:9][NH:8][C@H:13]([CH3:14])[CH2:12][N:11]1[CH2:15][C:16]1[CH:21]=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)[N:19]=[C:18]2[NH:29][N:30]=[C:31]([CH3:32])[C:17]=12

Participants

3

Reactant 1

HCID 136623188HCID 136623188, compound

Product 1

HCID 178434391HCID 178434391, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

585 mg 4-[4-((2S,5R)-4-benzyl-2,5-dimethyl-piperazin-1-ylmethyl)-3-methyl-1-(tetra-hydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol were dissolved in 10 ml methanol and 5 ml of THF and purged with argon. 50 mg Palladium (10% on charcoal) were added and the mixture was hydrogenated at r.t. for 15 h. The catalyst was filtered off and the solvents were evaporated. The residue was taken up in ethyl acetate and 1N aqueous hydrochloric acid. The phases were separated and the aqueous phase was washed with dichloromethane. To the aqueous phase was then added 1 ml concentrated aqueous hydrochloric acid and the reaction was left standing overnight. After freeze-drying 390 mg (90%) of the title compound were obtained.

Workup

  1. custom5 ml of THF and purged with argon
  2. addition50 mg Palladium (10% on charcoal) were added
  3. filtrationThe catalyst was filtered off
  4. customthe solvents were evaporated
  5. customThe phases were separated
  6. washthe aqueous phase was washed with dichloromethane
  7. additionTo the aqueous phase was then added 1 ml concentrated aqueous hydrochloric acid
  8. waitthe reaction was left
  9. waitstanding overnight
  10. dry with materialAfter freeze-drying 390 mg (90%) of the title compound
  11. customwere obtained

Sources & evidence

ORD record
ord-87fa343f8dc9415794e9890ce1505e1f
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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