반응 #169910

반응 방정식

toluene

N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-benzamide trifluoroacetate

toluene

→

desired product

수율 5.4%

N-(3-Bromo-4-fluorophenyl)-4-({4-[(1,1-dioxidothiomorpholin-4-yl)methyl]benzyl}amino)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide trifluoroacetate

수율 5.4%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도heated in the microwave at 130° C. for 10 min
2. 2
   기타The reaction mixture was quenched with acetic acid
3. 3
   농축concentrated
4. 4
   기타purified by preparative LCMS

실험 절차

A solution of N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-benzamide trifluoroacetate (20 mg, 28 μmol) in tetrahydrofuran (0.83 mL) was treated with 2.0 M of borane-dimethyl sulfide complex in toluene (42 μL, 85 μmol) was heated in the microwave at 130° C. for 5 min. The reaction mixture was treated with additional 2.0 M of borane-dimethyl sulfide complex in toluene (40 μL, 80 μmol) and heated in the microwave at 130° C. for 10 min. The reaction mixture was quenched with acetic acid, concentrated and purified by preparative LCMS to give the desired product (1 mg, 5%). LCMS for C21H23BrFN6O4S (M+H)+: m/z=553.0, 554.9.

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