Trifluoroacetic acid → HCID 66604678, compound

Participants

Reaction Steps

tert-Butyl 4-(1-carbamoyl-7-(morpholine-4-carbonyl)-9H-carbazol-3-yl)piperidine-1-carboxylate (Example 393, 50 mg, 0.099 mmol) was dissolved in 1,2-Dichloroethane (3 ml) and trifluoroacetic acid (1 ml, 12.98 mmol) and stirred for 1 hour at room temperature. Evaporation of volatiles and purification by reversed phase preparative HPLC, followed by filtration of product containing fractions through a PHENOMENEX® Strata-X cartridge (2 g adsorbent), a wash with Methanol, and elution with 2M NH3 in MeOH gave 21.9 mg 7-(morpholine-4-carbonyl)-3-(piperidin-4-yl)-9H-carbazole-1-carboxamide. MS (ESI) m/e−=405 and m/e=407 consistent with [M−H]− and [M+H]+. HPLC retention time 7.61 min. (Sunfire C18 3.5 μm, 4.6×150 mm column, 15 min gradient, 10-100% B, 1 mL/min. Solvent A: 5% CH3CN—95% H2O—0.1% TFA; Solvent B: 95% CH3CN—5% H2O—0.1% TFA). 1H NMR (CD3OD) δ ppm 8.21 (s, 1H), 8.20 (d, 1H, J=8.0), 7.87 (d, 1H, J=1.5), 7.69 (s, 1H), 7.27 (dd, 1H, J=8.0, 1.5), 3.90-3.50 (b, 8H), 3.23 (br. d., 2H, J˜12), 2.91 (m, 1H), 2.83 (m, 2H), 1.97 (br. d., 2H, J˜12), 1.85 (m, 2H).

Provenance & Evidence