HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (R)-6-bromo-4-(1-cyclopropylethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (R)-1-Cyclopropylethylamine | HCID 7016286 | — |
| Reactant | 6-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide | HCID 68291192 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | (R)-6-bromo-4-(1-cyclopropylethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide | HCID 68291753 | 84.2% |
Reaction Steps
A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 474.3 mg, 1.728 mmol), (R)-1-cyclopropylethylamine (162 mg, 1.901 mmol) and DIPEA (0.453 mL, 2.59 mmol) in NMP (Volume: 5 mL) was heated to 100° C. for 4 hr. The reaction was cooled and 10 mL of water was added and the resulting mixture was stirred for 10 minutes. The solid was collected by vacuum filtration and dried to afford the title compound (470 mg, 80%). HPLC (Method N): retention time=3.258 min. LC/MS (M+H)+=325.1. 1H NMR (400 MHz, CD3OD) δ 8.11 (s, 1H), 7.60 (dd, J=1.8, 0.7 Hz, 1H), 6.94 (d, J=1.8 Hz, 1H), 4.12-3.73 (m, 1H), 1.39 (d, J=6.4 Hz, 3H), 1.18-1.04 (m, 1H), 0.64-0.49 (m, 2H), 0.41-0.27 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221826B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-8e797c668dcd4d38a87012150ea0b365 |
| Source note | uspto-grants-2015_12 |