HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (S)-methyl 3-(4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoro-methyl)phenoxy)ethyl)piperidin-1-yl)-2-hydroxypropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl (2S)-2-oxiranecarboxylate | HCID 10942355 | — |
| Reactant | 1-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile 2,2,2-trifluoroacetate | HCID 86673347 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (S)-methyl 3-(4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoro-methyl)phenoxy)ethyl)piperidin-1-yl)-2-hydroxypropanoate | HCID 70945180 | — |
Reaction Steps
(S)-Methyl oxirane-2-carboxylate (1.837 mmol, 0.188 g), 1-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile 2,2,2-trifluoroacetate (0.918 mmol, 0.5 g) and Hunig's base (1.837 mmol, 0.304 ml, 0.237 g) were heated in Methanol (5 ml) to 100° C. for 10 minutes in the microwave. The reaction mixture was concentrated in vacuo. The resulting residue was purified by column chromatography, eluting with DCM—90/10 DCM/MeOH to afford (S)-methyl 3-(4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoro-methyl)phenoxy)ethyl)piperidin-1-yl)-2-hydroxypropanoate. (0.34 g)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115126B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-508742002a5048a8a5f69143c92b5a7d |
| Source note | uspto-grants-2015_08 |