Triethylamine → HCID 19601669, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-iodophenyl)-N-methyl-N-(3-hydroxypropyl)-3-isoquinolinecarbo-xamide (20 mg, 0.045 mmol), DMAP (5.5 mg, 0.045 mmol), and Et3N (0.02 mL, 0.14 mmol) in CH2Cl2 (2 mL) at 0° C. was added dropwise MsCl (0.006 mL, 0.77 mmol). The resulting mixture was stirred at 0° C. and monitored by TLC. After stirring at 0° C. for 4 h, TLC showed that no starting material left. Then, it was transferred into separatory funnel and washed with H2O (15 mL) The organic layer was dried (MgSO4), and filtered. The filtrate was concentrated in vacuo. The residue was purified on column (silica gel, 2% MeOH/CH2Cl2, 0.1% Et3N), thereby affording an oil (16 mg, 68%). 1H NMR (CDCl3) d 2.12-2.22 (m, 2 H, CH2), 2.77, 3.06 (two s, total 3 H, --SO2Me), 3.17, 3.20 (two s, total 3 H, N--Me), 3.62-3.82 (m, 2 H, N--CH2), 4.15 (t, J=6.0 Hz, 1 H, CH2O), 4.39 (t, J=6.0 Hz, 1 H, CH2O), 7.19-7.27 (m, 1 H, aromatic), 7.39-7.41 (m, 1 H, aromatic), 7.48-7.64 (m, 3 H, aromatic), 7.73-7.79 (m, 1 H, aromatic), 7.96-8.05 (m, 2 H, aromatic), 8.12, 8.24 (two s, total 1 H, aromatic). HRFABMS Cacld. for C21H21ILiN2O4S: 531.0427 (M+Li)+. Found: 531.0443.

Provenance & Evidence