HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}ethyl)-7-(methyloxy)pyrido[2,3-b]pyrazin-2(1H)-one Hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,1-Dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)(1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-4-piperidinyl)carbamate | HCID 57815243 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}ethyl)-7-(methyloxy)pyrido[2,3-b]pyrazin-2(1H)-one Hydrochloride | HCID 68991133 | 23% |
Reaction Steps
A solution of 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)(1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-4-piperidinyl)carbamate (1.408 g, 2.551 mmol) in chloroform (20 ml) and MeOH (5 ml) was added 4M HCl in 1,4-dioxane (10 ml) and the reaction was stirred at rt for 0.5 h before evaporation, treatment with sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×100 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the free base of the title compound as a yellow solid (266 mg, 23%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071592B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-d15f298dd7bd4937ab254ad34cca4da4 |
| Source note | uspto-grants-2011_12 |