HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Cyanobenzoic acid → HCID 71697354, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Cyanobenzoic acid | HCID 12087 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione | HCID 1249836 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 71697354 | HCID 71697354 | 92.1% |
Reaction Steps
To a solution of 4-cyanobenzoic acid (46 mg, 0.31 mmol) in 3 mL of DMF was added DIPEA (131 μL, 0.75 mmol) followed by HBTU (114 mg, 0.30 mmol). After being stirred at room temperature for 1 h, compound 76 (101 mg, 0.25 mmol) was added and then the reaction mixture was stirred at room temperature overnight. The reaction solution was diluted with 50 mL of ethyl acetate and washed with water (30 mL×5), collected the organic layer, dried over Na2SO4, filtered, concentrated and purified by silica column chromatography (15% ethyl acetate in hexanes) to afford 97 mg (92.1%) of the title compound 25d as a light-yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115122B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-0c635c75a3f4491f93ce82daa957a13d |
| Source note | uspto-grants-2015_08 |