HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 117842945, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 3-Oxetanone | HCID 15024254 | — |
| Reactant | HCID 117842917 | HCID 117842917 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | HCID 117842945 | HCID 117842945 | 22.2% |
Reaction Steps
(R)-4-((R)-1-((3-methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (130 mg, 0.31 mmol) was dissolved in THF (7.71 ml), followed by the addition of Hunig's base (0.05 ml, 0.31 mmol), 3-oxetanone (0.2 ml, 3.08 mmol), sodium triacetoxyborohydride (228.79 mg, 1.08 mmol) and stirred at 50 C for 90 minutes. The reaction was diluted with 25% methanol/dichloromethane, washed with water, dried, filtered and concentrated. Residues were purified by silica gel column chromatography to yield the (R)-4-((R)-1-((3-methyl-6-(6-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-3-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (32.9 mg, 22%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376441B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-1434fb4f08a04e3e996bf98e58605517 |
| Source note | uspto-grants-2016_06 |