Diisopropylethylamine → (E)-methyl 3-(4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzamido)propanoate

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Reaction Steps

The (E)-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzoic acid compound 57a (100.0 mg, 0.170 mmol) was treated with β alanine methyl ester (59.1 mg, 0.420 mmol), HATU (96.4 mg, 0.250 mmol), DIEA (0.175 mL, 1.00 mmol) in DMF (2 mL), and the mixture was stirred at rt for 3 h. The reaction was diluted with DCM and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with MeOH, filtered and dried to give (E)-methyl 3-(4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzamido)propanoate which was subjected to saponification with LiOH, using the methods described in Example 15, Step C, to afford the title compound 39. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.54-2.57 (m, 1H), 3.46-3.57 (m, 3H), 3.77-3.88 (m, 4H), 4.26-4.36 (m, 4H), 7.46-7.51 (m, 1H), 7.56 (t, J=7.5 Hz, 1H), 7.65 (d, J=16.1 Hz, 1H), 7.70-7.91 (m, 5H), 7.96 (t, J=9.3 Hz, 2H), 8.00-8.11 (m, 2H), 8.25-8.30 (m, 1H), 8.35 (d, J=8.6 Hz, 1H), 8.75 (s, 1H). Mass Spectrum LCMS, ESI (pos.) Calcd. for C31H28N6O4: 572.2 [M+H]. found 572.5.

Provenance & Evidence