Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | n,n-Dimethylpiperazine-1-carboxamide | HCID 712909 | — |
| Reactant | HCID 1777704 | HCID 1777704 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 71279061 | HCID 71279061 | 55% |
Reaction Steps
A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.050 g, 0.18 mmol) obtained in Example A1, Step 1 in ethanol (2.0 mL) was added with piperazine-1-carboxylic acid dimethylamide (0.035 g, 0.22 mmol), and 37% aqueous formaldehyde (0.020 g, 0.24 mmol), and the mixture was stirred overnight at 80° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)-N,N-dimethylpiperazine-1-carboxamide (0.044 g, 55%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156827B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-3c1d700663214651a0709636cada5b54 |
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| Source note | uspto-grants-2015_10 |
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