HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Methyl N-(6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl)-N-methylglycinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Glycine, N-methyl-, methyl ester, hydrochloride (1:1) | HCID 83544 | — |
| Reactant | 2-Chloro-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]-pyridine-3,5-dicarbonitrile | HCID 86649641 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl N-(6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl)-N-methylglycinate | HCID 66672288 | — |
Reaction Steps
230 mg (about 0.45 mmol) of the crude product from Example 50A were dissolved in 3 ml of absolute THF, and 127 mg (0.91 mmol) of methyl sarcosinate hydrochloride and 138 mg (1.36 mmol) of triethylamine were added. The reaction mixture was stirred at RT for 10 h. After removal of the solvent on a rotary evaporator, the residue was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gave the product as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609686B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-085deab682e14926a8856ba10b48100a |
| Source note | uspto-grants-2013_12 |