HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4-(1-{4-[4-(2-Methanesulfonyl-ethyl)-piperazin-1-yl]-2-methyl-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | 1-(2-(Methylsulfonyl)ethyl)piperazine | HCID 3801959 | — |
| Reactant | 4-[1-(4-iodo-2-methyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester | HCID 57496369 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 4-(1-{4-[4-(2-Methanesulfonyl-ethyl)-piperazin-1-yl]-2-methyl-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester | HCID 57496310 | 6% |
Reaction Steps
A solution of 4-[1-(4-iodo-2-methyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (78 mg, 0.15 mmol), 1-(2-methanesulfonyl-ethyl)-piperazine (0.75 mmol, 5.0 eq), CuI (0.15 mmol, 1 eq), L-proline (0.27 mmol, 1.8 eq), and potassium carbonate (0.15 mmole, 1 eq) in DMSO (2 mL) was heated at 120° C. for 1 hour under microwave conditions. The crude was purified through prep-LCMS 5-95% to provide Compound A223 as a brown sticky oil (5 mg, 6%). Exact mass calculated for C28H39N7O5S 585.3, found LCMS (ESI) m/z 586.6 (M+H+, 90%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410119B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-00058e7902584f4d938ce24c2be3ebeb |
| Source note | uspto-grants-2013_04 |