HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Methylpropylamine → Methyl 3-bromo-5-(methyl(propyl)carbamoyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Methylpropylamine | HCID 12315 | — |
| 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 | 3-Bromo-5-(methoxycarbonyl)benzoic acid | HCID 22593641 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Methyl 3-bromo-5-(methyl(propyl)carbamoyl)benzoate | HCID 57529325 | 99% |
Reaction Steps
A mixture of 3-bromo-5-(methoxycarbonyl)benzoic acid (1.0 g, 3.86 mmol) and HATU (1.76 g, 4.63 mmol) in DMF (35 mL) was stirred at room temperature for 10 min. Then N-methylpropan-1-amine (0.28 g, 0.4 mL, 3.86 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with H2O (3 times) and brine, dried over sodium sulfate, and concentrated under vacuum to give the title compound (1.2 g, 99% yield): HPLC retention time: 1.89 min (method A). MS (ESI) (M+H)+ 314.03.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07476764B2 |
| Source dataset | uspto-grants-2009_01 |
| ORD ID | ord-0e9b3be59a034d37870358af773d3cad |
| Source note | uspto-grants-2009_01 |