Trifluoroacetic acid → HCID 19601674, compound

Participants

Reaction Steps

To a solution of 1-(2-iodophenyl)-N-methyl-N-(3-triphenylmethoxy-propyl)-3-isoquinolinecarboxamide (107 mg, 0.16 mmol) in CH2Cl2 (10 mL) was added dropwise TFA (1 mL). The mixture was stirred at room temperature for 40 min. Then it was transferred into a separatory funnel and washed with saturated NaHCO3 solution (2×10 mL), water (20 mL), and brine (20 mL), then dried (MgSO4), and filtered. After removing the solvent in vacuo, the residue was purified on column (silica gel, 2% MeOH/CH2Cl2, 0.1% Et3N), thereby affording starting material (5.2 mg) and the titled compound (51.2 mg, 73%). mp 51-52° C. 1H NMR (CDCl3) d 1.78-1.95 (m, 2 H, CH2), 3.12, 3.19 (two s, total 3 H, N--Me), 3.52-3.74 (m, 3 H), 3.82-4.32 (m, 2 H), 7.19-7.31 (m, 1 H, aromatic), 7.35-7.42 (m, 1 H, aromatic), 7.48-7.63 (m, 3 H, aromatic), 7.72-7.81 (m, 2 H, aromatic), 8.17, 8.26 (two s, total 1 H, aromatic). HRMS Cacld. for C20H19IN2O: 446.0491. Found: 446.0501.

Provenance & Evidence