Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidin-4-ol | HCID 79341 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | HCID 66616329 | HCID 66616329 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 46864296 | HCID 46864296 | 67.1% |
Reaction Steps
A solution of 4-{4-[8-(3-methanesulfonyl-propoxy)-imidazo[1,2-a]pyridine-3-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid (0.09 g) in DMF (3 mL) was treated with BOP (0.126 g), and the mixture stirred at RT for 15 min DIEA (0.1 mL) and piperidin-4-ol (29 mg) were added, and the mixture stirred at RT overnight. The reaction mixture was then diluted with water and stirred at RT for 30 min, permitting the product to precipitate. The resulting solid was filtered, washed with water, dried, and titurated with EtOAc. The product was filtered, dried at 50° C. under vacuum overnight to provide (4-hydroxy-piperidin-1-yl)-(4-{4-[8-(3-methanesulfonyl-propoxy)-imidazo[1,2-a]pyridin-3-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone (compound 5, 71 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08569306B2 |
|---|
| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-ba0a02280db94d54b0931fdb5c3bb844 |
|---|
| Source note | uspto-grants-2013_10 |
|---|