Sodium Hydroxide → 8-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid

Temperature

60 °C

A suspension of 8-(4-cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (150 mg, 0.46 mmol) and 1M NaOH (1.5 mL, 1.5 mmol) in IMS (2 mL) was heated at 60° C. for 2 hours. The reaction mixture was then cooled to room temperature, diluted with water and glacial acetic acid was added to adjust pH to 4. The precipitate was filtered off and dried in a drying pistol at 40° C. for 18 hours to afford the title compound as a cream solid (154 mg, 99%). 1H NMR (DMSO-d6):10.53 (1 H, s), 8.34 (1 H, s), 7.74 (1 H, d, J=7.3 Hz), 7.35 (1 H, t, J=8.3 Hz), 7.24 (1 H, d, J=11.2 Hz), 7.13(1 H, d, J=8.1 Hz), 7.01 (1H, d, J=9.3 Hz), 6.23 (1H, s), 3.61 (1 H, m), 2.38 (2 H, m), 2.14 (2 H, m), 1.99 (1 H, m), 1.84 (1 H, m).

1. temperatureThe reaction mixture was then cooled to room temperature
2. additionwas added
3. filtrationThe precipitate was filtered off
4. customdried in a drying pistol at 40° C. for 18 hours

ORD record

ord-df9576cb03bc417c95ec96e9ba311390

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293763B2