HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-(2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Trifluoroacetate | HCID 84468 | — |
| Reactant | (S)-3-Oxiranyl-pyridine | HCID 13319559 | — |
| Reactant | (R)-N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide | HCID 69456022 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | N-(2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetyl)methanesulfonamide | HCID 69712472 | — |
Reaction Steps
A mixture of (R)—N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide.trifluoroacetate (40 mg, 0.091 mmol), (R)-(pyridin-3-yl)oxirane (48 mg, 0.36 mmol) and iPr2NEt (24 μL, 0.137 mmol) in acetonitrile (1 mL) is refluxed for 3 hours. After cooling, the mixture is concentrated and purified by preparative reversed phase HPLC (trifluoroacetic acid/water/acetonitrile) to give the desired N-(2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetyl)methanesulfonamide.2 trifluoroacetate (3 mg, yield: 3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07217724B2 |
| Source dataset | uspto-grants-2007_05 |
| ORD ID | ord-a447bf8daa8f42e1b7b3a9c9676a3f12 |
| Source note | uspto-grants-2007_05 |