HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (5S)-5-({[6-(2-Cyclopropylpyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl]sulfonyl}methyl)-5-methylimidazolidine-2,4-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chloride | HCID 16738713 | — |
| Reactant | 6-[2-(Cyclopropyl)pyrimidin-5-yl]-1,2,3,4-tetrahydroisoquinoline | HCID 66734853 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium chloride dihydrate | HCID 23713072 | — |
| Product | (5S)-5-({[6-(2-Cyclopropylpyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl]sulfonyl}methyl)-5-methylimidazolidine-2,4-dione | HCID 59164389 | 54.7% |
Reaction Steps
[(4S)-4-Methyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride (0.020 g, 0.087 mmol) in anhydrous THF (0.40 mL) was added dropwise to a stirred solution of 6-[2-(cyclopropyl)pyrimidin-5-yl]-1,2,3,4-tetrahydroisoquinoline (0.023 g, 0.091 mmol), DIPEA (0.022 mL, 0.13 mmol) and dry THF (0.50 mL) at RT. After the addition was complete, the solution was stirred at RT for 2 h and then taken up in water-brine and extracted twice with EtOAc. The combined organic phases were washed with brine, dried, filtered and concentrated to give a crude product. Purification by preparative HPLC afforded 0.021 g (50%) of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07655664B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-fecda251a1884e5aa75e4b466a604b18 |
| Source note | uspto-grants-2010_02 |