HCID 178434409, compound → HCID 178434408, compound

HRID 2279132Notes

Reaction equation

HRID 2279132 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[C:16]([CH3:18])([CH3:17])[CH2:15][N:14]([CH2:19][C:20]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]=3[F:33])[N:23]=[C:22]3[NH:34][N:35]=[C:36]([CH3:37])[C:21]=23)[C:13]([CH3:39])([CH3:38])[CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[F:33][C:27]1[CH:28]=[C:29]([OH:32])[CH:30]=[CH:31][C:26]=1[C:24]1[N:23]=[C:22]2[NH:34][N:35]=[C:36]([CH3:37])[C:21]2=[C:20]([CH2:19][N:14]2[CH2:15][C:16]([CH3:17])([CH3:18])[N:11]([CH2:10][CH2:9][OH:8])[CH2:12][C:13]2([CH3:39])[CH3:38])[CH:25]=1

Participants

4

Reactant 1

HCID 178434409HCID 178434409, compound

Product 1

HCID 178434408HCID 178434408, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

63 mg of 4-{4-[4-(2-Benzyloxy-ethyl)-2,2,5,5-tetramethyl-piperazin-1-ylmethyl]-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl}-3-fluoro-phenol were dissolved in 5 ml of methanol. 2 mg of Pd/C (10%) were added and the mixture was hydrogenated for 5 h at 5 bar. Then 1 ml of hydrorchloric acid (1M in dioxane) was added and the mixture was again hydrogenated at 5 bar for 24 h. The reaction was filtrated and concentrated in vacuo. After purification by HPLC 1 mg of the title compound was obtained.

Workup

  1. waitthe mixture was again hydrogenated at 5 bar for 24 h
  2. filtrationThe reaction was filtrated
  3. concentrationconcentrated in vacuo
  4. customAfter purification by HPLC 1 mg of the title compound
  5. customwas obtained

Sources & evidence

ORD record
ord-2034bd836a384c89adfaa57f1b8e6f90
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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