Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 90415230 | HCID 90415230 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 90414805 | HCID 90414805 | 87% |
Reaction Steps
To a solution of ethyl 1-((5-(3-chlorophenyl)-6-methoxypyridin-3-yl)methyl)-1H-pyrazole-4-carboxylate (Example 169, 25.00 mg, 0.07 mmol) in THF (2 mL), methanol (2 mL) was added lithium hydroxide (1.00 mL, 1.00 mol/L, 1.00 mmol). The mixture was stirred at room temperature for 2 h. The solvents were removed under reduced pressure and the crude residue dissolved in water. The aqueous reaction mixture was acidified with 1 N HCl (5 mL), and extracted into ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title compound (20 mg, 87%). 1H NMR (400 MHz, DMSO-d6) δ 12.30 (br s, 1H), 8.39 (br s, 1H), 8.19 (br s, 1H), 7.80 (br s, 2H), 7.68-7.26 (m, 4H), 5.34 (br s, 2H), 3.87 (br s, 3H). [M+H]=344.31.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09120770B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-7d6c31737b4945cf876e50149a5f6b67 |
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| Source note | uspto-grants-2015_09 |
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