Sodium hydride → N-(2,4-dimethylphenyl)-N-isobutyl-4-(((tetrahydro-2H-pyran-4-yl)methoxy)methyl)benzenesulfonamide

Temperatur

20 °C

To a solution of crude 4-(bromomethyl)-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (100 mg, 0.122 mmol) and (tetrahydro-2H-pyran-4-yl)methanol (14.15 mg, 0.122 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (1 mL) and dimethyl sulfoxide (DMSO) (0.5 mL) was added sodium hydride (approximately 4.87 mg, 0.122 mmol, 60% dispersed in oil) in one charge. The reaction mixture was stirred at 20° C. for 16 hours. The reaction was then quenched with methanol (0.5 mL) and water (0.5 mL) and concentrated in vacuo to give a residue in DMSO. This was diluted with dichloromethane (10 mL) and water (10 mL) and stirred vigorously for 10 minutes. The layers were separated by hydrophobic frit and the organic fraction evaporated to give the crude product. The sample was then purified by mass directed autoprep (formic acid modifier). The appropriate fractions were concentrated under a stream of nitrogen to give the required product, 4.2 mg. LCMS [LCMS1] Rt 1.44 min, m/z (ES+) 446 (M+H).

1. additioncharge
2. customThe reaction was then quenched with methanol (0.5 mL) and water (0.5 mL)
3. concentrationconcentrated in vacuo
4. customto give a residue in DMSO
5. stirringstirred vigorously for 10 minutes
6. customThe layers were separated by hydrophobic frit
7. customthe organic fraction evaporated
8. customto give the crude product
9. customThe sample was then purified by mass
10. concentrationThe appropriate fractions were concentrated under a stream of nitrogen

ORD-Eintrag

ord-9506c3f27c74452791882c3d7d25c153

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09428452B2