Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 2-(2-Aminoethyl)-2H-isoquinolin-1-one | HCID 66960500 | — |
| Reactant | 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde | HCID 86670476 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 70657140 | HCID 70657140 | 80.9% |
Reaction Steps
2-(2-Aminoethyl)-2H-isoquinolin-1-one (1.0 g) was added to a methanol solution (15 ml) of 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde (1.46 g). The mixture was stirred for 0.5 hours at room temperature. Sodium borohydride (0.23 g) was added to the mixture, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using dichloromethane. The organic layer was washed with water and saturated saline, dried with magnesium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→8:2). The purified product was condensed under reduced pressure to give the title compound (1.92 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08822453B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-af15ea9e12f042afa0a83a3398039a66 |
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| Source note | uspto-grants-2014_09 |
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