Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | HCID 178465998 | HCID 178465998 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | HCID 178465999 | HCID 178465999 | 49.2% |
Reaction Steps
A mixture of 2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)-N-(3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-yl)acetamide (100 mg, 0.170 mmol) in TFA.DCM (solvate) (10 mL, 10%) was stirred for 0.5 h at 25° C. Then the mixture was concentrated to give a residue which purified by preparative HPLC (column: ASB C18 150*25 mm/Mobile phase A: Water(Water+0.1% HCl)/Mobile phaseB: Acetonitrile/Gradient: 33-63 (B %)/Flowrate: 25 mL/min/Run time: 15 min) to yield a white solid of 2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-yl)acetamide hydrochloride (43.33 mg, 0.084 mmol, 49.2% yield): 1H NMR (400 MHz, DMSO-d6) δ 11.81 (s, 1H), 10.68 (s, 1H), 7.46-7.28 (m, 5H), 7.11 (d, J=2.0 Hz, 1H), 6.41 (s, 1H), 4.03 (q, J=6.8 Hz, 2H), 3.66 (s, 2H), 1.45 (s, 6H), 1.32 (t, J=6.9 Hz, 3H). ES-LCMS m/z 467 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09382238B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-48566bfad9224d86b13b3e4727af6e03 |
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| Source note | uspto-grants-2016_07 |
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