Tetrabutylammonium Fluoride → HCID 54589186, compound

Participants

Reaction Steps

To a solution of N-(4-(4-(3-(3-tert-butyl-1-(3-chloro-4-(triisopropylsilyloxy)phenyl)-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)morpholine-4-carboxamide (70 mg, 0.078 mmol) in dry THF (2.0 mL) was added TBAF (1.0 M in THF, 116 μL, 0.116 mmol) and the reaction mixture kept at RT for 16 hr. The reaction mixture was diluted with MeOH (1.0 mL) and after 5 min was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 4 g, EtOAc in isohexane, 0-100%, gradient elution) to afford the title compound, Example 12, as a pink solid (20 mg, 39%); Rt 3.97 min (Method 1 basic); m/z 655 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) δ: 1.27 (9H, s), 3.36 (4H, m), 3.52 (4H, m), 6.37 (1H, s), 6.61 (1H, dd), 7.12 (1H, d), 7.31 (1H, d), 7.35 (1H, dd), 7.37 (1H, d), 7.54 (1H, d), 7.57 (1H, m), 7.64 (1H, m), 7.84 (1H, d), 7.91 (1H, br s), 8.06 (1H, d), 8.12 (1H, d), 8.74 (1H, s), 9.09 (1H, s), 9.26 (1H, s), 10.62 (1H, br s).

Provenance & Evidence