Methanol → HCID 22100287, compound

Participants

Reaction Steps

To a solution of 3-(N-benzylaminocarbonyl)-4-methyl-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperazine (29 mg, 0.06 mmol) in THF (5 mL) at room temperature, under nitrogen, was added borane-THF (1.0 mL of a 1.0M solution in THF, 1.0 mmol). The mixture was heated at reflux for 18 h, then cooled to room temperature. MeOH (2 mL) was added and the solvents evaporated. The residue was dissolved in EtOH (10 mL), and K2CO3 (17 mg, 0.13 mmol) was added. The mixture was heated at 75° C. for 20 h, before the solvent was evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH:NH3 (95:5:1), to afford the amine (12 mg, 45%) as a gum. The title compound was characterised as its hydrogen oxalate salt. 1H nmr (360 MHz, d6 -DMSO) δ 1.80-1.96 (2H, m), 2.31 (3H, s), 2.37-2.62 (4H, m), 2.66-2.79 (3H, m), 2.80-3.06 (6H, m), 3.98 (1H, d, J=13.4 Hz), 4.03 (1H, d, J=13.4 Hz), 7.28-7.50 (8H, m), 7.78 (1H, s), 9.02 (2H, s), 11.12 (1H, br s). MS (ES+) 444 (M+1).

Provenance & Evidence