HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 6-chloro-4-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}ethyl)-1,2,4-benzotriazin-3(4H)-one 1-oxide Hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,1-Dimethylethyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]-4-piperidinyl}(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)carbamate | HCID 86635336 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 6-chloro-4-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}ethyl)-1,2,4-benzotriazin-3(4H)-one 1-oxide Hydrochloride | HCID 86635337 | 167.1% |
Reaction Steps
A solution of 1,1-dimethylethyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]-4-piperidinyl}(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)carbamate (81 mg, 0.141 mmol) in chloroform (1 ml) and MeOH (1 ml) was added 4M HCl in 1,4-dioxane (1 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 foam (60 mg, 90%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071592B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-0774355e45e446838a113ab157bf5376 |
| Source note | uspto-grants-2011_12 |