Triethylamine → HCID 25261851, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 67C (33 mg, 0.14 mmol) in tetrahydrofuran (0.3 mL), was added triethylamine (28 mg, 0.27 mmol). After shaking a solution of p-nitrophenyl carbamoyl chloride (28 mg, 0.14 mmol) was added in tetrahydrofuran (0.3 mL). A precipitate was formed and after shaking for 30 minutes a solution of 4-methylcyclohexanamine (21 mg, 0.19 mmol) in tetrahydrofuran (0.6 mL) was added. The mixture was heated to 50° C. overnight. The mixture was cooled to ambient temperature, and filtered through Si-Carbonate cartridge, washed with methanol checked by LC/MS and concentrated to dryness. The residue was dissolved in 1:1 DMSO/Methanol and purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-6.0 min linear gradient 10-100% A, 6.0-7.0 min 100% A, 7.0-8.0 min linear gradient 100-10% A) to afford the title compound. 1H NMR (500 MHz, DMSO/D2O) δ ppm 0.83-0.93 (m, 3H), 0.93-1.01 (m, 1H), 1.15-1.25 (m, 1H), 1.26-1.35 (m, 10H), 1.41-1.99 (m, 10H), 3.59-3.67 (m, 2H), 3.75-3.80 (m, 1H), 3.96-4.08 (m, 1H), 4.19-4.32 (m, 2H); MS (ESI) m/z 381 (M+H)+.

Provenance & Evidence