HCID 68085472, compound → HCID 66604497, compound

Participants

Reaction Steps

tert-Butyl 4-(1-carbamoyl-7-(morpholine-4-carbonyl)-9H-carbazol-3-yl)-5,6-dihydropyridine-1(2H)−carboxylate (Example 390, 159 mg, 0.290 mmol) was dissolved in EtOH (50 ml) in a 500-ml PARR flask. The flask was flushed with nitrogen, than palladium (10% on carbon, 96 mg, 0.090 mmol) was added, the flask flushed with nitrogen again, then transferred onto PARR shaker and hydrogenated for 24 hours under 60 psi of hydrogen. The reaction mixture was filtered through a 0.45 uM nylon filter and concentrated in vacuum. 94.3 mg crude tert-butyl 4-(1-carbamoyl-7-(morpholine-4-carbonyl)-9H-carbazol-3-yl)piperidine-1-carboxylate (colorless film) was isolated. 44.3 mg of the crude were purified by preparative HPLC to give 21.5 mg tert-butyl 4-(1-carbamoyl-7-(morpholine-4-carbonyl)-9H-carbazol-3-yl)piperidine-1-carboxylate. MS m/e+=507, m/e−505 consistent with [M−H]− and [M+H]+. 1H NMR (CD3OD) δ ppm 8.21 (s, 1H), 8.20 (d, 1H, J=8.0), 7.86 (d, 1H, J=1.5), 7.67 (s, 1H), 7.26 (dd, 1H, J=8.0, 1.5), 4.29 (bd, 2H, J=13.3), 3.90-3.50 (b, 8H), 2.95 (m, 3H), 1.96 (br. d. 2H, J˜12), 1.79 (dq, 2H, J=4.1, 12.6), 1.51 (s, 9H).

Provenance & Evidence