HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Methyl 4-(2-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-oxoethoxy)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one | HCID 2405875 | — |
| 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 | 4-(Carboxymethoxy)-benzoic acid 1-methyl ester | HCID 13816151 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 4-(2-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-oxoethoxy)benzoate | HCID 41667763 | 63.21% |
Reaction Steps
To a stirred solution of 2-chloro-1-(4-(naphthalen-2-yl-sulfonyl)piperazin-1-yl)ethanone (compound 4, 0.2 g, 0.64 mmol) and 2-(4-(methoxycarbonyl)phenoxy)acetic acid (134 mg, 0.64 mmol) taken in dry DCM (20 mL), DIPEA (495 mg, 3.86 mmol) followed by HATU (486 mg, 1.27 mmol) was added at room temperature and stirred overnight. The mixture was then diluted with DCM washed with water (2×10 mL) and brine (2×10 mL) The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to yield the title compound (0.189 g, 63.21%) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115086B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-477070aec43747ab92ee3363aca8bfc2 |
| Source note | uspto-grants-2015_08 |