Hydrochloric Acid → 1-(4-(7-Morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylic acid

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Reaction Steps

Methyl 1-(4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylate (Compound 441, 31 mg, 0.07 mmol) was dissolved in methanol, and 1N NaOH solution (1 ml) was then added. After 8 hours at room temperature, the mixture was acidified with 2N HCl to pH 1. The mixture was concentrated in vacuo. The residue was dissolved in DMSO, and was purified by preparatory HPLC (30-65% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound (6.9 mg, 23%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ=12.67-12.24 (m, 1 H), 10.98 (s, 1 H), 8.10 (d, J=2.3 Hz, 1 H), 7.98 (d, J=8.3 Hz, 2 H), 7.47 (d, J=8.3 Hz, 2 H), 7.41 (s, 1 H), 6.37 (d, J=2.3 Hz, 1 H), 3.85 (m, 2 H), 3.74 (m, 2 H), 1.56-1.45 (m, 2 H), 1.26-1.17 (m, 2 H); ESI-MS: m/z 408.4 (M+H)+.

Provenance & Evidence