Diisopropylethylamine → HCID 178504692, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (21 mg) is added to 2-(4-methanesulfonyl-phenyl)-pyrimidine-5-carboxylic acid (1-cyano-piperidin-4-yl)-cyclopropyl-amide (130 mg, Intermediate 22) and ethyldiisopropylamine (634) in ethanol (30 mL) and the mixture is refluxed for 4 h. Another 10 mg hydroxylamine hydrochloride is added and the mixture is refluxed for 1 h and stirred at room temperature for 12 h. The solvent is removed in vacuo and the residue is purified by preparative HPLC (MeOH/H2O/TFA) to yield 2-(4-methanesulfonyl-phenyl)-pyrimidine-5-carboxylic acid cyclopropyl-[1-(N-hydroxycarbamimidoyl)-piperidin-4-yl]-amide as an intermediate. Subsequently 50 mg of the aforementioned intermediate are added to tetrahydrofuran (10 mL) followed by ethyldiisopropylamine (28 μL) and cyclopropanecarbonyl chloride (10 μL). The mixture is stirred at room temperature for 3 h. Acetonitrile is added and the mixture is refluxed for 12 h. After removal of the solvents the residue is purified by HPLC (MeOH/H2O/ammonia) to yield the desired product. LC (method 16): tR=1.17 min; Mass spectrum (ESI+): m/z=509 [M+H]+.

Provenance & Evidence