HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-{4-[2-Amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-1-ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxylic acid | HCID 12624227 | — |
| Reactant | (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate | HCID 75951468 | — |
| Reactant | HCID 86700031 | HCID 86700031 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-{4-[2-Amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-1-ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxamide | HCID 86700042 | 74.2% |
Reaction Steps
DIPEA (601 μl) was added to a solution of 1-ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxylic acid (420 mg) and COMU (961 mg) in DMF (5.0 ml) at room temperature, and the mixture was stirred for 20 minutes. The compound obtained in Step 2 of Example 1 (610 mg) was added at room temperature. The mixture was stirred for 15 hours, followed by the addition of water. The organic layer was extracted with ethyl acetate, and then washed with water and brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->60:1 (v/v)] to give 700 mg of the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08933103B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-98f9aa1bc1d341618a4de461f97c2d41 |
| Source note | uspto-grants-2015_01 |