HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-({4-[2-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-3,4-dihydro-2H-chromene-7-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 4-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one | HCID 59568688 | — |
| Reactant | 4-Formyl-3,4-dihydro-2H-chromene-7-carbonitrile | HCID 77230703 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-({4-[2-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-3,4-dihydro-2H-chromene-7-carbonitrile | HCID 68071446 | — |
Reaction Steps
To a solution of 4-formyl-3,4-dihydro-2H-chromene-7-carbonitrile (50 mg, 0.27 mmol) in DCM (3 mL) was added 4-methyl-5-[2-(piperazine-1-yl)ethyl]-2-benzofuran-1(3H)-one (57 mg, 0.27 mmol), sodium triacetoxyborohydride (27.0 mg, 0.267 mmol) and DIPEA (57 mg, 0.27 mmol). The reaction was stirred under nitrogen at room temperature for 16 hours when LC-MS indicated product formation. The mixture was diluted with DCM and the product was isolated by flash chromatography. LC-MS (IE, m/z): 432 [M+1]+. (0.18 μM)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09073882B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-e6e51629f4e744359081e60d8e551e8f |
| Source note | uspto-grants-2015_07 |