Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Ethyl 1-(6-{2-[(2,4-dimethylbenzyl)oxy]-3-methylphenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate | HCID 67159648 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 1-(6-{2-[(2,4-Dimethylbenzyl)oxy]-3-methylphenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid | HCID 25231525 | — |
Reaction Steps
To a solution of the title compound from Example 15 Step C (12.0 mg, 0.023 mmol) in 1,4-dioxane (1.5 mL) was added lithium hydroxide (0.5 mL, 2.0 M in water, 1.00 mmol), and the resulting mixture was stirred at 50° C. After 30 min, the reaction mixture was rendered acidic by addition of aqueous hydrochloric acid, then was diluted with 1,4-dioxane and passed through a 0.45 micron syringe filter. Purification by reverse phase HPLC (40 to 100% acetonitrile in water, each with 0.1% v/v TFA) provided the title compound: LCMS m/z 482.8 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 8.30 (s, 1H), 8.08 (t, J=8.0 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.0 Hz, 1H), 7.45 (dd, J=8.0, 1.5 Hz, 1H), 7.35-7.32 (m, 1H), 7.18 (t, J=7.5 Hz, 1H), 6.91-6.86 (m, 3H), 4.52 (s, 2H), 2.27 (s, 3H), 2.21 (s, 3H), 2.06 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455638B2 |
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| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-bc240a67dd214a179cd73c6d4895c929 |
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| Source note | uspto-grants-2013_06 |
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