Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | HCID 1777704 | HCID 1777704 | — |
| Reactant | HCID 86681908 | HCID 86681908 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86681909 | HCID 86681909 | 45% |
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 (3.0 mL) was added with tert-butyl methyl[8-(methylamino)octyl]carbamate (0.074 g, 0.27 mmol), and 37% aqueous formaldehyde (0.017 g, 0.22 mmol), and the mixture was stirred overnight at 70° 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 tert-butyl (Z)-8-[({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)(methyl)amino]octyl(methyl)carbamate (0.045 g, 45%).
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-67f852e158484ded8a0227e97b4192b8 |
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| Source note | uspto-grants-2015_10 |
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