HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Methyl 4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino)phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Methyl 4-(3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-7-(2-methoxyethoxy)-6-quinolinecarboxylate | HCID 58931268 | — |
| Solvent | Water | HCID 962 | — |
| Product | Methyl 4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino)phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate | HCID 58931300 | — |
Reaction Steps
Methyl 4-{3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-7-(2-methoxyethoxy)-6-quinolinecarboxylate (3.2 g), cyclopropylamine (1.3 ml) and dimethylformamide (20 ml) were stirred together at 60° C. for 10 minutes. The mixture was returned to room temperature, water was added, and extraction was performed with ethyl acetate. Silica gel was added to the extract solution and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=50:1, 20:1) to obtain 2.26 g of the target substance as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07253286B2 |
| Source dataset | uspto-grants-2007_08 |
| ORD ID | ord-451ee5b114524c7fb809fb0d4aae9d3f |
| Source note | uspto-grants-2007_08 |