HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 2-ethoxy-4-methyl-N-(thiophene-2-yl-methyl)-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (2-Thienylmethyl)amine | HCID 34005 | — |
| 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-Ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid | HCID 66584048 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-ethoxy-4-methyl-N-(thiophene-2-yl-methyl)-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide | HCID 56848179 | 75% |
Reaction Steps
53 μl (0.5 mmol) thiophene methane amine, 172 mg (0.5 mmol) HATU and 165 μl (1.2 mmol) NEt3 were added consecutively to a solution of 123 mg (0.4 mmol) 2-ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid in THF (3 ml) and thereafter stirred for 16 h at RT. The solution was subsequently diluted with EtOAc and washed with a 4N aq. NH4CL sol., a 1M aq. Na2CO3 sol. and brine. The organic phase was dried over MgSO4, filtered through silica gel and concentrated in a vacuum. 116 mg (0.3 mmol, 72%) 2-ethoxy-4-methyl-N-(thiophene-2-yl-methyl)-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 2) was obtained as a residue. MS: m/z 395.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09073862B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-7bbcbee1f85b42939bbeaafaa08d93d9 |
| Source note | uspto-grants-2015_07 |