Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| 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 | 2-(5-Bromo-2-oxopyridin-1(2H)-yl)acetic acid | HCID 16778801 | — |
| Reactant | 7-Methoxyquinolin-4-amine | HCID 17039870 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 25018892 | HCID 25018892 | 12.9% |
Reaction Steps
To a solution of 7-methoxyquinolin-4-amine (0.275 g, 2 mmol) and 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetic acid (0.273 g, 1 mmol) in 5 mL of DMF at rt was added triethylamine (0.2 ml, 2 mmol) followed by HATU (0.7 g, 2 mmol) solid. The reaction was then heated up to 40° C. for 8 hours and was cooled to rt and diluted with 60 mL of EtOAc and 30 mL of satd. NaHCO3 solution. The organic phase was separated, washed with 30 mL of brine and dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc to 10% MeOH/EtOAc) to give a white solid (0.05 g, 11% yield). MS (ESI pos. ion) m/z (MH+): 388.0. Calc'd Exact Mass for C17H14BrN3O3: 387.02.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08314087B2 |
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| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-1d056b744fa448988d359847e6bcceb4 |
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| Source note | uspto-grants-2012_11 |
|---|
