HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 178472576, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| 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 | 3-acetyl-1H-pyrazole-5-carboxylic acid | HCID 16767346 | — |
| Reactant | (2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester | HCID 86682253 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178472576 | HCID 178472576 | 13.8% |
Reaction Steps
To a stirred solution of 3-acetyl-1H-pyrazole-5-carboxylic acid (50.9 mg, 330 μmol), HATU (125 mg, 330 μmol), and DIPEA (104 μL, 0.6 mmol) in DMF (0.6 mL, 7.7 mmol), was added (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (104 mg, 300 μmol). The resulting mixture was stirred at room temperature until the reaction was complete. The mixture was diluted with DCM and washed with saturated aqueous NaHCO3. The organics were dried over Na2SO4, and the solvent removed. Half of material was then purified by preparative HPLC to yield the title compound (20 mg) as a TFA salt. MS m/z [M+H]+ calc'd for C25H26ClN3O5, 484.16. found 484.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09108934B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-329c99848252416b89b54a5b87da169e |
| Source note | uspto-grants-2015_08 |