Reaction #157349

Reaction equation

HCl

1,4-dioxane

tert-butyl 4-(5-bromofuran-2-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

→

desired product

Yield 94.0%

(5-bromofuran-2-yl)(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)methanone dihydrochloride

Yield 94.0%

Solvents

MeOH

Conditions

Workup

1. 1
   Concentrationthe reaction mixture was concentrated under reduced pressure
2. 2
   Otherpurified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
3. 3
   ConcentrationThe desired chromatography fractions were concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONdissolved in MeOH (1 mL)
5. 5
   workup.ADDITIONtreated with 4 M HCl in 1,4-dioxane (6 mL)
6. 6
   ConcentrationThis was concentrated under reduced pressure

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(5-bromofuran-2-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (75 mg, 0.16 mmol) in MeOH (1 mL). After stirring overnight, 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 desired chromatography fractions were concentrated under reduced pressure, dissolved in MeOH (1 mL), and treated with 4 M HCl in 1,4-dioxane (6 mL). This was concentrated under reduced pressure, yielding 66 mg (94%) of the desired product as a white solid. LC-MS: RT=3.54 min, [M+H]+=366.0.

Source