Compound PK150

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)urea

From: Repurposing human kinase inhibitors to create an antibiotic active against drug-resistant Staphylococcus aureus, persisters and biofilms

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InChIKey SHPYXCLUNMOJOB-UHFFFAOYSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

The title compound was synthesised following the general procedure outlined for compound SFN-C. Yield: 91% (148 mg, 0.375 mmol); workup A (CH2Cl2/ MeOH = 99/1). TLC (CH2Cl2/ MeOH = 98/2): Rf = 0.57 [UV | PMA]. 1H NMR (500 MHz, DMSO-d6): δ [ppm] = 9.22 (s, 1H), 9.07 (s, 1H), 8.09 (d, J = 2.3 Hz, 1H), 7.68 – 7.59 (m, 3H), 7.33 (d, J = 8.7 Hz, 1H), 7.12 (dd, J = 8.8, 2.2 Hz, 1H). 13C NMR (126 MHz, DMSO-d6): δ [ppm] = 152.5, 142.8, 139.2, 137.8, 136.0, 132.0, 131.3 (t, J = 252.2 Hz), 126.7 (q, J = 30.5 Hz), 123.2, 122.8 (q, J = 273.1 Hz), 122.5 (m), 116.9 (q, J = 6.0 Hz), 114.2, 110.1, 101.7 (observed complexity is due to the C-F splitting). ESI-HR-MS (m/z) [M+H+] calcd. for C15H9ClF5N2O3+, 395.0216; found, 395.0211.

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