Water → HCID 86274185, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-methylpyrazolecarboxylic acid (0.069 g, 0.547 mmol) in thionyl chloride (1.50 mL, 20.66 mmol) was heated at 60° C. for 0.5 h, concentrated to dryness, treated with toluene and concentrated to dryness (3×). The residue was treated with a solution of Example C1 (0.150 g, 0.455 mmol) in pyridine (5 mL) and stirred at RT overnight. The mixture was treated with water, stirred for 0.5 h and the resulting solid collected via filtration. The material was suspended in MTBE, sonicated collected via filtration and purified via silica gel chromatography (MeOH/DCM) to afford 1-methyl-N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)-1H-pyrazole-4-carboxamide (128 mg, 64%). 1H NMR (400 MHz, DMSO-d6): δ 11.23 (s, 1H), 10.58 (s, 1H), 10.44 (s, 1H), 8.39 (s, 1H), 8.27 (d, J=2.9 Hz, 1H), 8.24 (d, J=5.7 Hz, 1H), 8.11-8.09 (m, 1H), 8.08 (d, J=0.7 Hz, 1H), 7.76-7.75 (m, 2H), 6.74 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 1.21 (s, 9H); MS (ESI) m/z: 438.2 (M+H+).

Provenance & Evidence