Acetic Acid → [3-(5-methyl-4-oxo-4,5-dihydro-3H-1,3,5,6-tetraaza-cyclopenta[a]naphthalen-2-yl)-cyclohexyl]-carbamic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

[3-(4-Amino-1-methyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester (55 mg, 0.122 mmol) was dissolved in glacial acetic acid (1.32 g, 22.02 mmol) and heated at 120° C. for 15 h. After cooing to room temperature, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography, eluting with 2% MeOH in CH2Cl2 to give 45 mg (85%) of [3-(5-methyl-4-oxo-4,5-dihydro-3H-1,3,5,6-tetraaza-cyclopenta[a]naphthalen-2-yl)-cyclohexyl]-carbamic acid benzyl ester as a white solid. 1H-NMR (CDCl3): δ 8.61 (m, 2H), 7.33 (m, 7H), 5.18 (m, 2H), 4.27 (m, 1H), 4.0 (s, 3H), 3.81 (m, 1H), 3.44 (m, 1H), 2.52 (m, 3H), 2.28 (m, 1H), 2.12 (m, 1H), 1.8 (m, 1H), 1.79 (m, 3H), 1.31 (m, 1H). MS: calculated for C24H25N5O3+H 432.2; found: 432.0.

Provenance & Evidence