Diisopropylethylamine → (4-Benzyl-2,2,5,5-tetramethyl-piperazin-1-yl)-[6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone

HRID 2279140Notes

Reaction equation

HRID 2279140 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([C:27]([OH:29])=O)[C:14]3[C:19]([CH3:20])=[N:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:15]=3[N:16]=2)=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.[CH2:39]([N:46]1[CH2:51][C:50]([CH3:53])([CH3:52])[NH:49][CH2:48][C:47]1([CH3:55])[CH3:54])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl.O>[CH2:39]([N:46]1[C:47]([CH3:55])([CH3:54])[CH2:48][N:49]([C:27]([C:13]2[CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=3)[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]=23)=[O:29])[C:50]([CH3:53])([CH3:52])[CH2:51]1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 308103HCID 308103, compoundHCID 900138076-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 90013965(4-Benzyl-2,2,5,5-tetramethyl-piperazin-1-yl)-[6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanoneYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1.24 g of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid in 15 ml of DCM were added 2.1 ml of Hünig's base, 1.03 g of BEP and 0.87 g of 1-Benzyl-2,2,5,5-tetramethyl-piperazine. The reaction was stirred at r.t. for 3 h. For workup it was diluted with water and DCM and the layers were separated. The organic layer was washed with water twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 1.54 g (81%) of the title compound.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, heptane/EtOAc gradient)

Sources & evidence

ORD record
ord-ae8886be63aa461fbb7aee87daac9488
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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