Triethylamine → HCID 58775940, compound

Participants

Reaction Steps

EDIC (0.33 mmol, 0.07 g) was added in one portion to a mixture of (4-amino-benzyl)-methyl-(tetrahydro-pyran -4-yl)-amine Compound 1d (0.25 mmol, 0.06 g), 1-methyl-1H-indole-2-carboxylic acid Compound 12a (0.22 mmol, 0.04 g) and HOBt (0.22 mmol, 0.03 g) in DMF (5.0 mL) at 0° C. The resulting suspension was warmed to r.t. and then a crystal of DMAP and Et3N (0.65 mmol, 0.11 mL) was added and the reaction mixture was stirred overnight. The resulting orange-yellow suspension was poured in water and was extracted with EtOAc (25 mL). The organic layer was washed with water (2×20 mL) followed by 5% NaOH solution (10 mL) and brine. The organic layer was separated, dried over Na2SO4 and filtered. The solvent was removed in vacuo and the resulting residue was purified by preparative TLC (15:1 CH2Cl2/MeOH) to yield 1-methyl-1H-indole-2-carboxylic acid (4-{[methyl-(tetrahydro-pyran -4-yl)-amino]-methyl}-phenyl)-amide Compound 12b as a pale yellow solid (0.05 g, 60%). MS m/e 378 (M+H, 100%).

Provenance & Evidence