HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetyl chloride → 1-{4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | N-Methyl-N-[(3S,4S)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine | HCID 12084830 | — |
| Solvent | Pyridine methylene chloride | HCID 21875418 | — |
| Product | 1-{4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanone | HCID 12084831 | 15% |
Reaction Steps
To a stirred solution of the product from Method C (0.03 grams, 0.114 mmol) dissolved in 5 mL of 10:1 dichloromethane/pyridine was added (0.018 grams, 0.228 mmol) of acetylchloride and the resulting mixture stirred at room temperature for 18 hours. The reaction mixture was then partitioned between dichloromethane and saturated sodium bicarbonate (NaHCO3). The organic layer was washed again with saturated NaHCO3, dried over sodium sulfate and concentrated to dryness in vacuo. The residue was purified by preparative thin layer chromatography (PTLC) (silica; 4% methanol in dichloromethane) affording 0.005 mg (15%) of the title compound as a colorless oil. LRMS: 288.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06956041B2 |
| Source dataset | uspto-grants-2005_10 |
| ORD ID | ord-96c5532bcfd84d9caf72a522be53dea0 |
| Source note | uspto-grants-2005_10 |