HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → (2-{3-Chloro-5-[(2-cyano-ethyl)-(tetrahydro-furan-2-ylmethyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 3-[(Tetrahydrofuran-2-ylmethyl)amino]propanenitrile | HCID 2779328 | — |
| Reactant | Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]- | HCID 18348849 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2-{3-Chloro-5-[(2-cyano-ethyl)-(tetrahydro-furan-2-ylmethyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester | HCID 69948292 | 96.5% |
Reaction Steps
To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.060 g), TBTU (0.096 g) and HOBT (0.030 g) in DMF (1 ml) was added DIPEA (0.052 ml) followed by 3-[(tetrahydro-furan-2-ylmethyl)-amino]-propionitrile (0.047 g) after 15 min. The reaction was stirred at room temperature for 96 h, and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.078 g) was obtained as a brown oil 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-049c9ee70cf34471943abadd9f445d0b |
| Source note | uspto-grants-2001_12 |