Sodium Hydroxide → 4-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-methoxybenzoate (126 mg, 0.22 mmol) in dioxane/H2O (8 mL/8 mL) was added NaOH (75 mg, 1.9 mmol), the reaction mixture was heated to 35° C. with stirring for 1 hour, the dioxane was removed in vacuo, and the aqueous layer was adjusted to pH=4-5 with conc. HCl, the precipitate was collected by filtration and washed with methanol (5 mL) to afford 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-methoxybenzoic acid (68 mg, 54.8%) as a off-white solid. 1H NMR (300 MHz, DMSO): δ 10.23 (s, 1H), 9.63 (s, 1H), 8.83 (s, 1H), 7.63 (d, 1H, J=2.1 Hz), 7.58 (d, 1H, J=8.4 Hz), 7.46 (s, 1H), 7.33 (dd, 1H, J1=8.7 Hz, J2=2.4 Hz), 7.14 (dd, 1H, J1=8.4 Hz, J2=1.5 Hz), 6.80-6.78 (m, 1H), 4.79 (d, 1H, J=11.7 Hz), 4.65 (d, 1H, J=12.6 Hz), 3.68-3.61 (m, 9H), 3.10-2.89 (m, 2H), 2.58-2.54 (m, 1H), 2.03-1.99 (m, 1H), 1.78-1.71 (m, 2H), 1.48-1.44 (m, 1H). LC-MS: 585 [M+H]+, tR=1.48 min. HPLC: 96.06% at 214 nm, 97.26% at 254 nm, tR=5.66 min.

Provenance & Evidence