Water → HCID 11660060, compound

Participants

Reaction Steps

A reaction mixture of 0.4 g (2.3 mMol) of the compound from example 104D in 4 mls of N,N-dimethylformamide, 0.85 mls (4.8 mMol) of N,N-diisopropylethylamine and 0.8 g (2.3 mMol) of the compound from example 24D was stirred at ambient temperature for 18 hours. 50 mls of water was added to the reaction and the precipitate collected by filtration. The precipitate was solubilized in ethyl acetate and the organic phase extracted with water and saturated NaCl. The organic phase was dried with MgSO4, filtered and the solvent evaporated. 2 mls of 5N NaOH in methanol was added to the residue and stirred at room temperature for 1 hour. 100 mls of ethyl acetate was added and the organic phase extracted with water and saturated NaCl. The organic phase was dried with MgSO4, filtered and the solvent removed, and the residue purified by flash chromatography using a gradient from dichloromethane to 10% methanol in dichloromethane with a few drops of NH4OH as the solvent system to provide the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.98 (s, 1 H) 8.78 (s, 1 H) 8.09 (s, 1 H) 7.64 (d, J=7.12 Hz, 1 H) 7.20 (t, J=7.97 Hz, 1 H) 7.05 (d, J=8.14 Hz, 1 H) 6.84-6.91 (m, 2 H) 6.59-6.71 (m, 2 H) 4.02-4.11 (m, 1 H) 3.36-3.51 (m, 2 H) 2.74-2.88 (m, 1 H) 2.62-2.74 (m, 1 H) 2.19 (s, 3 H) 1.91-2.04 (m, 1 H) 1.61-1.76 (m, 1 H). MS ESI m/z 337.1 (M+H)+.

Provenance & Evidence