1-Hydroxybenzotriazole → [3-(4-Amino-1-methyl-2-oxo-1,2-dihydro-quinolin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

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Reaction Steps

Following procedure described for example 3, step C, 3-benzyloxycarbonylamino-cyclohexanecarboxylic acid (0.586 g, 2.11 mmol), TEA (0.21 g, 2.11 mmol), HOBt (0.286 g, 2.11 mmol), and 3,4-diamino-1-methyl-1H-quinolin-2-one (0.40 g, 2.11 mmol) were reacted to give crude amide. Column chromatography purification of the crude product resulted in pure [3-(4-amino-1-methyl-2-oxo-1,2-dihydro-quinolin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester (0.22 g, 23% yield). 1H-NMR (CDCl3): δ 8.14 (m, 1H), 7.62 (d, 1H, J=8.4 Hz), 7.55 (t, 1H, J=3.2 Hz), 7.35 (m, 7H), 5.50 (s, 2H), 5.10 (m, 2H), 3.72 (s, 3H), 3.62 (m, 1H), 2.58 (m, 1H), 2.34 (m, 1H), 2.04 (m, 2H), 1.94 (m, 1H), 1.67 (m, 2H), 1.46 (m, 2H), 1.13 (m, 1H). MS: calculated for C25H28N4O4+H 449.2; found: 449.4.

Provenance & Evidence