Trifluoroacetic acid → HCID 59394712, compound

Participants

Reaction Steps

To a solution of tert-butyl (4-(1-(5-cyclopropyl-1-methyl-1H-pyrazol-3-ylcarbamoyl)-1H-indol-5-yloxy)pyridin-2-yl)methyl(methyl)carbamate (0.124 g, 0.240 mmol) in DCM (5 ml) is added TFA (2 ml, 0.240 mmol). The reaction is stirred for approximately 30 minutes and then concentrated in vacuo to near dryness. The residue is dissolved in DCM, diluted with water and neutralized via the addition of saturated aqueous NaHCO3. The resulting layers are then separated and the aqueous layer is extracted twice with DCM. The organic layers are combined dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue is purified via FCC (0-15% MeOH/DCM) to provide the title compound. MS (ESI) m/z 417.2 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.64-0.70 (m, 2 H) 0.96-1.02 (m, 2 H) 1.87-1.96 (m, 1 H) 2.27 (s, 3 H) 3.71 (s, 2 H) 3.80 (s, 3 H) 6.16 (d, J=0.51 Hz, 1 H) 6.73 (dd, J=3.79, 0.51 Hz, 1 H) 6.80 (dd, J=5.56, 2.53 Hz, 1 H) 6.93 (d, J=2.02 Hz, 1 H) 7.09 (dd, J=8.97, 2.40 Hz, 1 H) 7.42 (d, J=2.27 Hz, 1 H) 8.17 (d, J=3.54 Hz, 1 H) 8.33 (d, J=8.84 Hz, 1 H) 8.36 (d, J=5.81 Hz, 1 H).

Provenance & Evidence