HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-Methoxy-1-(4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-YL)piperidin-1-YL)ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methoxyacetic Acid | HCID 12251 | — |
| 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 | Tert-butyl 4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate | HCID 59373921 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-Methoxy-1-(4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-YL)piperidin-1-YL)ethanone | HCID 59374246 | — |
Reaction Steps
A solution of tert-butyl 4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate (0.220 g, 0.434 mmol) in DCM (5 mL) was added 4M HCl in dioxane (2 mL). After stirring for 2 h at RT, diisopropylethylamine (0.525 mL, 3.01 mmol), 2-methoxyacetic acid (0.077 mL, 1.004 mmol), and HATU (0.305 g, 0.803 mmol) was added and the reaction mixture was stirred at RT in 2 h. Water was added and the mixture was extracted with DCM (3×), dried over Na2SO4, concentrated. The crude material was purified by reverse phase HPLC, then neutralized with saturated NaHCO3, extracted with DCM (3×), dried over Na2SO4, concentrated to give the title compound. MS (ESI, pos. ion) m/z: 434.2 (M+1). IC50 (uM) 0.000058.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637500B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-faf8e295bf664ea2b982f9469b966620 |
| Source note | uspto-grants-2014_01 |