Réaction #157388

Équation de réaction

HCl

1,4-dioxane

tert-butyl 4-(6-methoxybenzo[d]oxazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate di-TFA salt

→

desired product

Rendement 44.0%

6-methoxy-2-(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)benzo[d]oxazole hydrochloride

Rendement 44.0%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   Concentrationthe reaction mixture was concentrated under reduced pressure
2. 2
   Autrepurified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
3. 3
   workup.ADDITIONThe fractions containing the desired product
4. 4
   workup.ADDITIONwas added
5. 5
   ExtractionThis was extracted with EtOAc (3×)
6. 6
   SéchageThe combined organics were dried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe material was dissolved in MeOH (1 mL)
10. 10
    workup.ADDITION4 M HCl in 1,4-dioxane (0.031 mL) was added
11. 11
    ConcentrationThe mixture was concentrated under reduced pressure

Mode opératoire

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(6-methoxybenzo[d]oxazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate di-TFA salt (150.6 mg, 0.225 mmol) in MeOH (1 mL). After 2 h, the reaction mixture was concentrated under reduced pressure and purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient). The fractions containing the desired product were brought to pH 12 with 1 N NaOH, and brine (20 mL) was added. This was extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was dissolved in MeOH (1 mL) and 4 M HCl in 1,4-dioxane (0.031 mL) was added. The mixture was concentrated under reduced pressure to give 37.4 mg (44%) of the desired product as the hydrochloride salt. LC-MS: RT=4.00 min, [M+H]+=341.1.

Source