N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide → N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 1, making variations as required to use N-benzyl-2-(5-bromopentanamido)-4-methylthiazole-5-carboxamide in replace of N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 35% yield: mp 175-176° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.33-7.25 (m, 5H), 5.96 (s, 1H), 4.57 (d, J=5.6 Hz, 2H), 4.13 (t, J=6.0 Hz, 2H), 2.66 (t, J=6.8 Hz, 2H), 2.64 (s, 3H), 2.02-1.87 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 169.8, 162.7, 156.9, 152.0, 138.0, 128.8, 127.9, 127.6, 119.4, 48.0, 44.0, 32.7, 22.5, 20.2, 17.4; MS (ES+) m/z 330.6 (M+1).

Provenance & Evidence