Triethylamine → HCID 90014402, compound

Participants

Reaction Steps

To a solution of 4-[(trifluoromethyl)sulfonyl]aniline (180 mg, 0.80 mmol) in 2 mL dichlroethane at 0° C. was added triethylamine (0.250 mL, 1.76 mmol) and triphosgene (71 mg, 0.24 mmol). The solution was allowed to stir at ambient temperature for 10 min. To the crude reaction mixture of {4-[(trifluoromethyl)sulfonyl]phenyl}carbamic chloride was added N-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]propan-2-amine (256 mg, 0.80 mmol) and the reaction was allowed to stir at ambient temperature for 16 h. The mixture was concentrated and partitioned between saturated NaHCO3 and ethylacetate. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The filtrate was concentrated and purified by silica gel chromatography to give 1-propan-2-yl-3-{4-[(trifluoromethyl)sulfonyl]phenyl}-1-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]urea (38%). LCMS [M+H]+=571.2.

Provenance & Evidence