Triethylamine → N-[4-chloro-2-[(E)-hydroxyiminomethyl]-5-[4-[3-(2-methoxyphenyl)-5-methyl-1,2-oxazole-4-carbonyl]piperazin-1-yl]phenyl]-4-(dimethylamino)benzamide

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Reaction Steps

The reaction mixture of N-(4-chloro-2-formyl-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)phenyl)-4-(dimethylamino)benzamide (Example 115, 7.7 mg, 0.013 mmol), hydroxylamine hydrochloride (1.8 mg, 0.026 mmol) and triethylamine (3.6 μL, 0.026 mmol) in DMF (1.2 mL), MeOH (0.240 mL) and DCM (0.240 mL) was stirred at RT overnight. The product was purified by preparative HPLC (10 mM NH4OAc AcCN/H2O) to give 2.7 mg of the title compound. 1H-NMR (DMSO-d6, 400 MHz) δ 11.46 (1H, br. s.), 8.48 (1H, s), 8.31 (1H, s), 7.87 (2H, d, J=9.0 Hz), 7.58 (1H, s), 7.55-7.44 (2H, m), 7.18 (1H, d, J=8.3 Hz), 7.10 (1H, t, J=7.5 Hz), 6.81 (2H, d, J=9.0 Hz), 3.75 (3H, s), 3.03 (6H, s). HPLC/MS (Method H): (ES+) m/z (M+H)+=617; Rt=1.98 min.

Provenance & Evidence