HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 308103 | HCID 308103 | — |
| Reactant | 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid | HCID 90013807 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (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 | HCID 90013965 | 81% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133181B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-ae8886be63aa461fbb7aee87daac9488 |
| Source note | uspto-grants-2015_09 |