Anisole → HCID 118308145, compound

Temperature

0 °C

To a solution of N-(4,4-difluoro-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl)-2-methylpropane-2-sulfonamide (45 mg, 0.11 mmol) in DCM (3 ml) at 0° C. was added anisole (CAS number 100-66-3; 0.22 ml, 2.01 mmol) followed by the drop wise addition of trifluoromethanesulfonic acid in DCM (0.2M, 2.5 ml, 0.500 mmol). The reaction mixture was stirred at 0° C. for 1 hour then at room temperature for 2 hours. A further portion of trifluoromethanesulfonic acid in DCM (0.2M, 0.5 ml, 0.100 mmol) was added, the reaction mixture stirred for another hour at room temperature then quenched with sodium hydroxide (0.1M) until pH 11 was obtained. The reaction mixture was then extracted with DCM. The organics were filtered through a hydrophobic frit and concentrated in vacuo. The crude material was purified by SCX chromatography (2M ammonia in methanol) to afford the title compound.

1. waitat room temperature for 2 hours
2. stirringthe reaction mixture stirred for another hour at room temperature
3. customthen quenched with sodium hydroxide (0.1M) until pH 11
4. customwas obtained
5. extractionThe reaction mixture was then extracted with DCM
6. filtrationThe organics were filtered through a hydrophobic frit
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by SCX chromatography (2M ammonia in methanol)

ORD record

ord-a67306288a404c05b7f48abc50c5c48f

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156829B2