HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(Methylamino)ethanol → 6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-N-(2-hydroxyethyl)-N-methyl-nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(Methylamino)ethanol | HCID 8016 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid | HCID 59240635 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-N-(2-hydroxyethyl)-N-methyl-nicotinamide | HCID 59240625 | 61% |
Reaction Steps
6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid (100 mg, 0.225 mmol), DMF (0.5 mL), Diisopropylethylamine (195 μL, 1.125 mmol), HBTU (102 mg, 0.270 mmol), and 2-(methylamino)ethanol (18 μL, 0.225 mmol) are combined in a 10 mL flask and stirred for 4 h at room temperature. Concentrate to remove DMF in vacuo. The residue is purified by flash chromatography on silica gel (0-25% MeOH/CH2Cl2 with 5% TEA) to afford the title compound (68.2 mg, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536168B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-e061af082f1a4af0bee37570ed4744d8 |
| Source note | uspto-grants-2013_09 |