HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-((1-(5-Chloropyrimidin-2-yl)piperidin-4-yl)oxy)-6-(piperidin-4-yl)benzo[d]thiazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tert-butyl 4-(2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate | HCID 67467599 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-((1-(5-Chloropyrimidin-2-yl)piperidin-4-yl)oxy)-6-(piperidin-4-yl)benzo[d]thiazole | HCID 67468280 | 95% |
Reaction Steps
To a solution of tert-butyl 4-(2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate (133 mg, 0.251 mmol) in CH2Cl2 (2.5 mL) was added TFA (0.2 mL, 2.5 mmol). The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with CH2Cl2 (5 mL) and washed with aq. NaOH (1 N, 3 mL) and brine. The organic layer was dried (Na2SO4), filtered, and concentrated to afford 2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)-6-(piperidin-4-yl)benzo[d]thiazole (102 mg, 0.237 mmol, 95% yield) as a pale yellow solid. LCMS (m/z)=430 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08940716B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-0027a0a816dc4cc2ae817ad5ebd78219 |
| Source note | uspto-grants-2015_01 |