Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopentylamine | HCID 2906 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-Fluoronicotinic Acid | HCID 242819 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 1447952 | HCID 1447952 | 14.3% |
Reaction Steps
6-Fluoronicotinic acid (300 mg, 2.13 mmol) and cyclopentylamine (0.84 mL, 8.50 mmol) were combined in anhydrous THF (5 mL) and triethylamine (0.59 mL, 4.25 mmol). The mixture was heated at 60° C. for 3 days. The mixture was concentrated under reduced pressure, and the residue was suspended in water. The aqueous mixture was brought to pH 3 with phosphoric acid. The resulting precipitate was collected by vacuum filtration, washed with water, and dried in a vacuum oven for 1 h at 50° C. to give the title compound as a solid (63 mg, 14%): HPLC MS RT=1.14 min, MH+=207.2; 1H NMR (DMSO-d6) δ: 12.29 (1H, broad s), 8.50 (1H, d), 7.73 (1H, dd), 7.29 (1H, d), 6.42 (1H, d), 4.16 (1H, broad s), 1.90 (2H, m), 1.67 (2H, m), 1.53 (2H, m), 1.43 (2H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08466283B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-0f07cf08fcd34efd8ae5c29526d96048 |
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| Source note | uspto-grants-2013_06 |
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