HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Methylbutylamine → Methyl 3-{[butyl(methyl)amino]carbonyl)-5-iodobenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Methylbutylamine | HCID 8068 | — |
| 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 | 3-Iodo-5-(methoxycarbonyl)benzoic acid | HCID 15840391 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 3-{[butyl(methyl)amino]carbonyl)-5-iodobenzoate | HCID 21086165 | — |
Reaction Steps
3-Iodo-5-(methoxycarbonyl)benzoic acid (1 g, 3.3 mmol) is dissolved in DMF (10 mL), and diisopropylethylamine (1.7 mL, 9.8 mmol), HATU (1.5 g, 3.9 mmol), and N-methylbutylamine (581 μL, 4.9 mmol) are added. The reaction stirred at room temperature 2 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40% ethyl acetate/hexane) provides the title compound. ESI MS m/z 376.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07727997B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-8da84dc1edd148bab8666c6537bcb486 |
| Source note | uspto-grants-2010_06 |