HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 90455837, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | tert-Butyl 3-(piperazin-1-yl)azetidine-1-carboxylate | HCID 19360775 | — |
| Reactant | HCID 117607186 | HCID 117607186 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 90455837 | HCID 90455837 | 46% |
Reaction Steps
To a stirred solution of 3-(5-bromo-4-chloro-2-methoxyphenyl)propanoic acid (350 mg, 1.2 mmol) in DMF (30 mL) at RT, tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate (317 mg, 1.3 mmol), BOP (731 mg, 1.4 mmol) and DIEA (461 mg, 3.6 mmol) were added and the mixture was stirred at RT for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1) to afford the desired product (285 mg, 46% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09227978B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-044f03d3032f4407b6ce681fe261a558 |
| Source note | uspto-grants-2016_01 |