HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (2-{3-Chloro-5-[(2-cyano-ethyl)-cyclobutyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]- | HCID 18348849 | — |
| Reactant | 3-(Cyclobutylamino)propionitrile | HCID 18348909 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2-{3-Chloro-5-[(2-cyano-ethyl)-cyclobutyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester | HCID 54411432 | 110.2% |
Reaction Steps
To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.030 g) and HATU® (0.058 g) in DMF (0.4 ml) was added DIPEA (0.040 ml) followed by a solution of 3-(cyclobutylamino)propionitrile (0.038 g) in DMF (0.6 ml) after 10 min. The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.042 g) was obtained as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06326386B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-3173a4c0c8e64ea5934c02d977bb8bed |
| Source note | uspto-grants-2001_12 |