HuagongsheHuagongshe Chemistry Print Report · For research reference only
6-Aminonicotinic acid → (6-Aminopyridin-3-yl)((3R,5S)-3,5-dimethylmorpholino)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 6-Aminonicotinic acid | HCID 18496 | — |
| 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 | (3R,5S)-3,5-Dimethylmorpholine | HCID 12638209 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (6-Aminopyridin-3-yl)((3R,5S)-3,5-dimethylmorpholino)methanone | HCID 86684570 | 27.6% |
Reaction Steps
To a solution of (3S,5R)-3,5-dimethylmorpholine (1.15 g, 10 mmol) in DMF (15 mL) was added HATU (3.8 g, 10 mmol), DIPEA (2.6 g, 20 mmol), and 6-aminonicotinic acid (1.38 g, 10 mmol) at room temperature. The reaction mixture was stirred for 18 h. It was then filtered and the filtrate was purified with Combiflash (A: 1% NH4HCO3/water, B: acetonitrile) to afford 320a (650 mg, 27%) as a yellow solid. MS-ESI: [M+H]+ 236.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238655B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-d57e86c478ba4129b28596e038c0b3dd |
| Source note | uspto-grants-2016_01 |