1,2-Dichloroethane → HCID 86710419, compound

To the stirred solution of 4-(4-chloro-2,5-difluorophenyl)-2-methylnicotinic acid (1.7 g, 4.02 mmol) in DMF (0.5 mL) was added DIEA (2.81 mL, 16.06 mmol), HOBT (1.230 g, 8.03 mmol), EDC (1.155 g, 6.02 mmol) at 0° C. followed by addition of methylamine hydrochloride (0.488 g, 7.23 mmol). After stirring for 10 min, the ice bath was removed and the reaction mixture was allowed to stir overnight. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate (10 mL) and washed with water (10 mL) followed by brine (10 mL). The organic layer was separated and dried over sodium sulphate, filtered, and concentrated under reduced pressure to afford 4-(4-chloro-2,5-difluorophenyl)-N,2-dimethylnicotinamide (1 g, 2.123 mmol, 53% crude yield) as a brown solid which was taken to the next step without purification. LC/MS (ESI) m/e 297.3 [(M+H)+, calcd for C14H12ClF2N2O 297.1]; LC/MS retention time (method B): tR=0.76 min.

1. customthe ice bath was removed
2. stirringto stir overnight
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. additionThe residue was diluted with ethyl acetate (10 mL)
5. washwashed with water (10 mL)
6. customThe organic layer was separated
7. dry with materialdried over sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-0df27f30549547e7b8d264071482baac

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2