Triethylamine → HCID 57708173, compound

Participants

Reaction Steps

To a solution of 1-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropan-2-amine (step G, 38 mg, 0.1 mmol) in dichloromethane (1.5 mL) were added triethylamine (28 μL, 0.2 mmol) and 4-nitrophenyl chloroformate (24 mg, 0.12 mmol) at 0° C. The mixture was stirred for 4 h at room temperature. To the resulting mixture was added ammonium hydroxide solution (25% in water; 20 μL, 0.12 mmol) and stirred continue to 20 h. The reaction was quenched by addition of saturated sodium 6 bicarbonate aqueous solution (10 mL) and water (10 mL). The organic phase was separated and the aqueous layer was extracted with dichloromethane (10 mL×2). The combined organic layer was washed with water (20 mL×4), brine (10 mL) and dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel TLC eluting with dichloromethane/methanol (10/1) to afford 16 mg (38%) of the title compound.

Provenance & Evidence