HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 8-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine | HCID 97740 | — |
| Reactant | 8-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-one | HCID 58008558 | — |
| Reactant | (S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one | HCID 58008747 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | 8-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-one | HCID 58008558 | 60% |
| Product | HCID 178423766 | HCID 178423766 | — |
Reaction Steps
3-(1-Aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 4704) (200 mg, 0.72 mmol), 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (344 mg, 1.44 mmol) and DIPEA (279 mg, 2.16 mmol) were dissolved in n-BuOH (20 ml), and the resulting mixture was stirred at reflux for 16 h. The reaction mixture was concentrated in vacuo and purified by flash column chromatography on silica gel (eluting with 30% to 50% Hex/EA) to afford the desired product, 8-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one (compound 4901) (207 mg, 60% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08785456B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-8f444f6bf09a4d5691ca2783873cb94e |
| Source note | uspto-grants-2014_07 |