HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-(1-cyanocyclopropyl)-3-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1 (s)-(4-fluorophenyl)ethylamino]propionamide
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 | 1-Amino-1-cyclopropanecarbonitrile hydrochloride | HCID 14586363 | — |
| Reactant | 3-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethylamino]propionic acid | HCID 86600268 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-(1-cyanocyclopropyl)-3-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1 (s)-(4-fluorophenyl)ethylamino]propionamide | HCID 11387282 | 70% |
Reaction Steps
To a solution of 3-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethylamino]propionic acid (157 mg, 0.325 mmol) in DMF (5 mL) was added 1-aminocyclopropanecarbonitrile hydrochloride (46.4 mg, 0.39 mmol), HATU (186.3 mg, 0.49 mmol) and DIPEA (63.2 mg, 0.49 mmol). After 1 h, the reaction mixture was extracted with ethyl acetate (100 mL) and washed with satured NaHCO3 and brine. After driying with MgSO4, the solvent was removed and the residue was purified by column chromatograph yield the title compound (125 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07547701B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-73b40cc7457a4bbf95243848dcd8296d |
| Source note | uspto-grants-2009_06 |