HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 3-bromo-N-[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Benzoyl chloride, 3-bromo- | HCID 74377 | — |
| Reactant | N-[5-(6-aminoimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide | HCID 67983095 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3-bromo-N-[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]benzamide | HCID 67983168 | 42.8% |
Reaction Steps
An 8-mL vial is charged with N-[5-(6-aminoimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide (0.097 g, 0.3 mmol), 3-bromobenzoyl chloride (0.059 mL, 0.45 mmol), pyridine (0.073 mL), and MeCN (1.0 mL). The mixture is stirred at room temperature for 16 hours, concentrated onto celite and purified by silica gel chromatography (0-100% 1:0.1 EtOAc:MeOH in CH2Cl2) to give the title compound (0.065 g). LCMS (m/z)=506.4 and 508.4 [M+H]+, tR=2.96 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08871767B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-9b49c023e2b647139a6026422712fbaf |
| Source note | uspto-grants-2014_10 |