HuagongsheHuagongshe Chemistry Print Report · For research reference only
6-Chloronicotinic acid → 5-(Azetidin-1-ylcarbonyl)-2-chloropyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 6-Chloronicotinic acid | HCID 79222 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Azetidine hydrochloride | HCID 12308726 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-(Azetidin-1-ylcarbonyl)-2-chloropyridine | HCID 53629615 | 105.7% |
Reaction Steps
Commercially available 6-chloronicotinic acid (160 mg, 1.01 mmol) was dissolved in dichloromethane (5 mL), and azetidine hydrochloride (130 mg, 1.39 mmol), HATU (420 mg, 1.10 mmol) and N,N-diisopropylethylamine (0.50 mL, 2.87 mmol) were added, followed by stirring at room temperature overnight under nitrogen atmosphere. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-50%) to afford the desired compound (210 mg, yield ˜100%) as a colorless liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08017610B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-752f21d0432040e78e54dcb8e8ee4a3c |
| Source note | uspto-grants-2011_09 |