Ethylamine hydrochloride → HCID 57377301, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid with 1 eq. lithium chloride (54 mg, 0.133 mmol), ethylamine hydrochloride (44 mg, 0.534 mmole), diisopropyl-ethylamine (93 ul, 0.534 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 197 ul, 0.334 mmol) in tetrahydrofurane (3 ml) is stirred for 1.5 hours at 70° C. As no dissolution occurs after this time, ethylamine hydrochloride (87 mg, 1.07 mmol), diisopropylethylamine (186 ul, 1.07 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 99 ul, 0.167 mmol) are added and the mixture is stirred overnight at room temperature. The white suspension is diluted with ethyl acetate, washed once with water, once with sat. aqueous sodium bicarbonate solution, once with brine, dried with magnesium sulfate and the solvent is evaporated to dryness affording N4-ethyl-1-methyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (30 mg, 57.7%) as a white solid. mp.: 253-5° C. MS: m/z=390.2 (M+H+).

Provenance & Evidence