Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Piperidinemethanol | HCID 420771 | — |
| Reactant | HCID 58547777 | HCID 58547777 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 58547731 | HCID 58547731 | 17% |
Reaction Steps
To a mixture of 2-(3-((5-bromo-2-chloropyrimidin-4-yl)oxy)azetidin-1-yl)quinoline (see PREPARATION P2.11; 0.1 g, 0.25 mmol) and piperidin-4-yl-methanol (0.028 g, 0.25 mmol) was added DMSO (2 mL) and triethylamine (0.05 g, 0.50 mmol). The solution was heated to 150° C. under microwave for 3 hours. The mixture was then extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in hexanes) to give the title product (0.02 g, 0.04 mmol, 17% yield) as white solid. ESI-MS (M+1): 471 calc. for C22H24BrN5O2 470.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08497265B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-c8b162fc3f5c4352b5061100cd1f8670 |
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| Source note | uspto-grants-2013_07 |
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