HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 71258388, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Propanesulfonyl chloride, 2-methyl- | HCID 182236 | — |
| Reactant | HCID 71258404 | HCID 71258404 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71258388 | HCID 71258388 | 62% |
Reaction Steps
rac-1-[(3R,4R)-4-Methylpiperidin-3-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (23 mg, 0.056 mmol) in dichloromethane (2 mL) was mixed with N,N-diisopropylethylamine (30 μL, 0.17 mmol) and 2-methylpropane-1-sulfonyl chloride (12 μL, 0.092 mmol) under cooling with ice and stirred at room temperature for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol=1/1/0→0/10/1 (v/v/v)) to give the title compound as a pale pink solid (18.3 mg, yield 62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216999B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-b7cbda1755ba43648d62bb10076f405b |
| Source note | uspto-grants-2015_12 |