Water → Methyl 1-(4-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylate

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Reaction Steps

4-(1-(Methoxycarbonyl)cyclopropyl)benzoic acid (200 mg, 0.91 mmol) was suspended in CH2Cl2 (5 ml). At 0° C., oxalyl chloride (0.50 ml, 1.0 mmol) was then added, followed by 2 drops of DMF. The mixture was warmed to room temperature. After 2 hours, an additional amount of oxalyl chloride (0.15 ml) was added. After the reaction was completed, 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 200 mg, 0.91 mmol) in pyridine (5 ml) was added. After the reaction was complete, water was added and the volatiles were removed in vacuo. The aqueous residue was extracted with EtOAc 3 times. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by preparatory HPLC (65-80% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a yellow powder (96 mg, 24% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.27 (s, 1 H), 8.08-8.04 (m, 2 H), 8.04-7.99 (m, 2 H), 7.96 (s, 1 H), 7.66-7.60 (m, 3 H), 7.52-7.48 (m, 2 H), 6.40 (s, 1 H), 3.57 (s, 3 H), 2.40 (s, 3 H), 1.56-1.50 (m, 2 H), 1.31-1.25 (m, 2 H); ESI-MS: m/z 427.4 (M+H)+.

Provenance & Evidence