Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,2,2-Trifluoroethyl trifluoromethanesulfonate | HCID 80366 | — |
| Reactant | HCID 86677719 | HCID 86677719 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71509957 | HCID 71509957 | 20% |
Reaction Steps
To a mixture of 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-azetidin-3-yl-4-methoxy-2-methylbenzonitrile dihydrochloride (20 mg, 0.04 mmol) and triethylamine (20 μL, 0.14 mmol) in methylene chloride (0.3 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (11 mg, 0.049 mmol). The resulting mixture was stirred at 40° C. for 3 h. The solvents were evaporated and the crude material purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give 3.4 mg (20%) of the desired product. The product was isolated as a racemic mixture. LCMS calculated for C22H23F5N7O (M+H)+: m/z=496.2; Found: 496.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09199982B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-f87900cf98f945068018bb1644e546e6 |
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| Source note | uspto-grants-2015_12 |
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