Diisopropylethylamine → HCID 58864391, compound

Participants

Reaction Steps

A solution of 5-(2-amino-2-methoxycarbonyl-ethyl)-indazole-1-carboxylic acid tert-butyl ester (307 mg, 0.96 mmol), N,N-disuccinimidyl carbonate (246 mg, 0.961 mmol), and N,N-diisopropylethylamine (0.67 mL, 3.84 mmol) in methylene chloride was stirred for 30 min at room temperature. 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (238 mg, 1.03 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The solvent was evaporated and the residue subjected to flash chromatography using methylene chloride/methanol/triethylamine (93:5:2) as eluent, giving the product (259 mg, 47%). 1H-NMR (CDCl3, 300 MHz) δ 8.13–8.10 (m, 2H), 7.48 (br s, 1H), 7.31 (dd, J=8.8, 1.6 Hz, 1H), 7.16 (t, J=8.0 Hz, 1H), 7.05 (d, J=7.0 Hz, 1H), 6.94 (t, J=7.7 Hz, 1H), 6.82 (s, 1H), 6.66 (d, J=8.0 Hz, 1H), 4.98 (d, J=7.7 Hz, 1H), 4.87–4.81 (m, 1H), 4.58–4.49 (m, 1H), 4.26 (s, 2H), 4.05–3.97 (m, 2H), 3.74–3.67 (m, 4H), 3.29–3.23 (m, 2H), 2.93–2.84 (m, 2H), 1.76–1.62 (m, 1H), 1.70 (s, 9H), 1.48–1.42 (m, 1H). Mass spec.: 577 (MH)+.

Provenance & Evidence