HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(p-Tolyl)propionic acid → N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-3-p-tolyl-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(p-Tolyl)propionic acid | HCID 73927 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 5-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one | HCID 59579453 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-3-p-tolyl-propionamide | HCID 24784833 | 40% |
Reaction Steps
5-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one (50 mg, 0.2 mmol), HATU (99 mg, 0.26 mmol), 3-(4-methylphenyl)propionic acid (42 mg, 0.26 mmol) and DIPEA (110 mg, 0.86 mmol) were stirred in methylene chloride (3 mL) at room temperature for 16 hours. The mixture was purified via flash chromatography (12 g of silica gel, 0-10% MeOH/CH2Cl2 gradient) gave N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-3-p-tolyl-propionamide as a white solid (31 mg, 0.08 mmol, 40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546579B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-57b2d5dd8c9e40c2aed88ac63ff33698 |
| Source note | uspto-grants-2013_10 |