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 | HCID 67133798 | HCID 67133798 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 59486212 | HCID 59486212 | 65% |
Reaction Steps
134 μl (1.3 mmol) thiophenemethanamine, 438 mg (1.1 mmol) HATU and 420 μl (3.0 mmol) NEt3 were added in succession to a solution of 330 mg (1.05 mmol) 2-(ethylthio)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid (VVV08) in THF (8 ml) and the mixture was then heated for 24 h at 50° C. Then it was diluted with EE and washed with a 4M aqueous NH4Cl solution, a 1M aqueous Na2CO3 solution and brine. The organic phase was dried over MgSO4 and then filtered through a silica layer. Column chromatography (hexane/EE 7:3) of the residue yielded 277 mg (0.67 mmol, 65%) 2-ethylsulfanyl-4-methyl-N-(thiophen-2-yl-methyl)-7-(trifluoromethyl)-quinoline-3-carboxamide. MS: m/z 411.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08399673B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-12b53aa9a3dd4806ad4e23a92b26d7f1 |
|---|
| Source note | uspto-grants-2013_03 |
|---|
