HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 178456944, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Methyl-1-benzofuran-2-carboxylic acid | HCID 600591 | — |
| 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 178456897 | HCID 178456897 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178456944 | HCID 178456944 | 98.9% |
Reaction Steps
To a solution of (5Z)-4-(prop-2-yn-1-ylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (500 mg) in DMF (10 mL) were added N-ethyl-N-(1-methylethyl)propan-2-amine (1.40 mL), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (708 mg), and 3-methylbenzofuran-2-carboxylic acid (335 mg). The reaction mixture was stirred at room temperature overnight, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (625 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08772277B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-5059a52e0cca4cc7a02567d927865f92 |
| Source note | uspto-grants-2014_07 |