Hydrochloric Acid → 3-(7-(3-(2-(Methoxymethyl)pyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid hydrochloride

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Reaction Steps

Methyl 3-(7-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate (100 mg, 0.21 mmol) and NaOH (100 mg, 2.5 mmol) in 3 mL of 1,4-dioxane and 3 mL of H2O was stirred at room temperature for 3 hours and then treated by conc. HCl until pH=3-4. The solvent was removed under reduce pressure the residue 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: 50% acetonitrile/50% water (0.1% TFA V/V) initially, and then proceed to 80% acetonitrile/20% water (0.1% TFA V/V) in a linear fashion after just 9 min.) to give 3-(7-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid hydrochloride (30 mg, 31%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.28 (s, 1H), 9.41 (s, 1H), 8.98 (s, 1H), 6.62 (d, 1H, J=7.5 Hz), 8.08 (d, 1H, J=7.5 Hz), 7.66-7.62 (m, 2H), 7.47 (brs, 1H), 7.28 (brs, 1H), 3.95 (brs, 1H), 3.54-3.51 (m, 2H), 3.32-3.27 (m, 2H), 3.19 (s, 3H), 2.03-1.19 (m, 4H). LC-MS: 462 [M+H]+, tR=1.66 min. HPLC: 96.12% at 214 nm, 96.76% at 254 nm, tR=6.84 min.

Provenance & Evidence