HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,5-Dibromo-1-methylpyridin-2(1H)-one → 5-Bromo-1-methyl-3-(5-(3-methylazetidin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,5-Dibromo-1-methylpyridin-2(1H)-one | HCID 3614350 | — |
| Reactant | 5-(3-Methylazetidin-1-yl)pyridin-2-amine | HCID 58043963 | — |
| Reactant | tert-Butyl 4-(4-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)piperidine-1-carboxylate | HCID 58043998 | — |
| Product | 5-Bromo-1-methyl-3-(5-(3-methylazetidin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one | HCID 58043910 | 44% |
Reaction Steps
Using the same procedure as described for the preparation of 121a, a reaction of 236b (1.04 g, 6.40 mmol) with 3,5-dibromo-1-methylpyridin-2(1H)-one (1.90 g, 7.12 mmol) afforded a 44% yield (980 mg) of 236c as a brown solid: mp 135-136° C.; 1H NMR (500 MHz, DMSO-d6) d 8.49 (d, 1H, J=5.5 Hz), 8.42 (s, 1H), 7.50 (d, 1H, J=4.5 Hz), 7.41 (d, 1H, J=7.0 Hz), 7.20 (d, 1H, J=14.5 Hz), 6.85 (dd, 1H, J=14.5, 5.0 Hz), 3.91 (m, 2H), 3.49 (s, 3H), 3.34 (m, 2H), 2.75 (m, 1H), 1.21 (d, 3H, J=11.5 Hz; MS (ESI+) m/z 350.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618107B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-85900dc367dc48c2bf5e2d2d8db65c03 |
| Source note | uspto-grants-2013_12 |