Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | HCID 57489614 | HCID 57489614 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57489612 | HCID 57489612 | 85.5% |
Reaction Steps
A solution of 6-chloro-5-fluoro-2-(4-fluorophenylamino)nicotinamide (50 mg, 0.176 mmol) and piperidine (1 mL, 10.12 mmol) was sealed in a small microwave vial and heated in a heating block at 100° C. for 2 hrs. The reaction mixture was diluted with CH2Cl2 and washed with bicarbonate and water. The reaction mixture was concentrated and the dark crude material was chromatographed (ISCO Companion 40 g silica gel column and eluted with (90:9:1 CH2Cl2:MeOH: NH4OH)t/CH2Cl2 gradient (20-100%)) to give 50 mg of 5-fluoro-2-(4-fluorophenylamino)-6-(piperidin-1-yl)nicotinamide as a brown solid. LCMS: (M+H)+=333.21. 1H NMR (400 MHz, CDCl3) δ ppm 10.68 (1H, s), 7.52-7.57 (2 H, m), 7.22 (1H, d, J=14.06 Hz), 6.94-7.00 (2H, m), 5.47 (2H, br. s.), 3.64 (4H, d, J=6.15 Hz), 1.62-1.72 (6H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586751B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-056cb50f86cd456faccf043a141dbe51 |
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| Source note | uspto-grants-2013_11 |
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