Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 89462935 | HCID 89462935 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 136507783 | HCID 136507783 | — |
Reaction Steps
To a solution of ethyl 3-(5-amino-4-cyano-3-(pyridine-3-yl)-1H-pyrazol-1-yl)propanoate (213 mg, 0.75 mmol) in THF (5 mL) was added n-BuLi (0.6 mL, 1.49 mmol) at −60° C. The resulting mixture was stirred at −60° C. for 3 hours. 2 mL of water was added to quench the reaction and the THF was removed in vacuo. The residue was purified by HPLC to afford the desired product: MS (m/z): 240.1 [M+H]+, 1H NMR (DMSO, 400 MHz): δ11.79 (s, 1 H), 8.99 (s, 1 H), 8.65 (d, 1 H, J=5.2 Hz), 8.17 (d, 1 H, J=8.4 Hz), 7.57 (dd, 1 H, J=8.4 Hz, J=5.2 Hz), 4.38 (t, 2 H, J=7.6 Hz), 2.89 (t, 2 H, J=7.6 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09351973B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-f784949c81864d10ba6162f5c945b737 |
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| Source note | uspto-grants-2016_05 |
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