Triethylamine → (E)-N-(Methylsulfonyl)-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzamide hydrochloric acid salt

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Reaction Steps

To the suspension of compound 57a (160 mg, 0.33 mmol) in DCM (20 mL) was added oxalyl chloride (1.67 mL, 3.35 mmol) dropwise followed by a drop of DMF. The mixture was stirred at rt overnight under an Argon atmosphere. The reaction mixture was concentrated and the orange solid obtained was redissolved in DCM (20 mL). To this solution was added methanesulfonamide (63.7 mg, 0.670 mmol), Et3N (139 μL, 1.00 mmol) and DMAP (40.9 mg, 0.335 mmol). The mixture was stirred at rt for 12 h and concentrated. The residue was dissolved in DCM and extracted with 1N HCl, resulting in an emulsion. The emulsion was concentrated to obtain a residue which was then triturated with MeOH, collected by filtration, and dried to give the title compound 62. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.43 (s, 3H), 3.80-3.88 (m, 4H), 4.29-4.45 (m, 4H), 7.55 (s, 1H), 7.78-7.95 (m, 4H), 8.04 (t, J=7.6 Hz, 1H), 8.15 (d, J=8.3 Hz, 2H), 8.19-8.30 (m, 3H), 8.30-8.40 (m, 3H), 8.95 (d, J=8.6 Hz, 1H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C29H26N6O4S: 555.2 [M+H]. found 555.4.

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