Sodium Hydroxide → HCID 66551737, compound

Participants

Reaction Steps

To a stirred solution of 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoate (80 mg, 0.14 mmol) in 5 mL of THF and 5 mL of methanol was added a solution of 1N NaOH (5 mL) at room temperature. After the addition, the reaction was stirred at this temperature for 16 hours. The solvent was evaporated and the residue was diluted with water and adjusted to pH=2 by HCl (aq.). The suspension was filtered and dried. The crude was purified by preparative HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 ml/inj, flow rate: 20 ml/min; wavelength: 214 nm and 254 nm; the gradient conditions are: 20% acetonitrile/80% water (0.1% TFA V/V) initially, and then proceed to 55% acetonitrile/45% water (0.1% TFA V/V) in a linear fashion after just 9 min) to give 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoic acid (30 mg, 39%) as white solid. 1H NMR (300 MHz, DMSO): δ 9.66 (s, 1H), 8.83 (s, 1H), 8.74-8.72 (m, 1H), 7.88 (brs, 1H), 7.66 (d, 1H, J=7.8 Hz), 7.50-7.46 (m, 3H), 6.91 (d, 1H, J=8.7 Hz), 4.59 (brs, 1H), 3.87 (s, 4H), 3.76-3.72 (m, 8H), 2.27 (brs, 1H), 2.09 (brs, 1H). LC-MS: 550.8 [M+H]+, tR=1.38 min. HPLC: 98.09% at 214 nm, 96.40% at 254 nm, tR=4.64 min.

Provenance & Evidence