HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-N-(1-methylpiperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-3-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | 4-Amino-1-methylpiperidine | HCID 2737531 | — |
| Reactant | 3-Fluoro-4-((3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy)aniline | HCID 67221003 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-N-(1-methylpiperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-3-amine | HCID 68516372 | 51.4% |
Reaction Steps
A mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.10 g, 0.20 mmol; prepared as in Example 7, Step B), 1-methylpiperidin-4-amine (0.070 g, 0.61 mmol), (S)-pyrrolidine-2-carboxylic acid (9.4 mg, 0.82 mmol), CuI (7.8 mg, 0.041 mmol), and K2CO3 (0.14 g, 1.0 mmol) was heated in DMSO (4 mL) with sealed tube at 100° C. for 17 hours. The reaction mixture was cooled to ambient temperature and treated with CH2Cl2, washed with water, dried over MgSO4, and concentrated to give crude material which was purified by silica gel flash column chromatography (10% MeOH in CH2Cl2) to afford 49 mg (50%) of the desired product. LRMS (ESI pos) m/e 477.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07723330B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-a018ce4b46614091a7eab0ddd9320a9d |
| Source note | uspto-grants-2010_05 |