6-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrido[2,3-b]pyrazine → 6-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 510138

Reaction equation

HRID 510138 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[CH:15]=[CH:16][C:17]3[C:18]([N:23]=2)=[N:19][CH:20]=[CH:21][N:22]=3)=[N:6]1>CO.[Pt](=O)=O>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[CH:15]=[CH:16][C:17]3[NH:22][CH2:21][CH2:20][NH:19][C:18]=3[N:23]=2)=[N:6]1

Participants

4

Reactant 1

HCID 666142136-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrido[2,3-b]pyrazine

Product 1

HCID 569287396-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

80 mg (0.22 mmol) of the compound from example 68 were initially charged in methanol (4 ml), then 12 mg (0.045 mmol) of platinum(IV) oxide were added and the reaction mixture was hydrogenated at standard pressure overnight. The reaction mixture was filtered through Celite and the filtercake was washed with methanol. The filtrate was concentrated to give 79 mg (92% purity, 90% of theory) of the title compound, which were converted without further purification.

Workup

  1. customwas hydrogenated at standard pressure overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe filtercake was washed with methanol
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fde0969b986f48069664c46ed83d5242
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Linked notes

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