Dichloromethane → HCID 71714955, compound

Participants

Reaction Steps

Dess-Martin periodinane reagent (22.67 mg, 0.053 mmol) was added to a mixture of methyl 2-(hydroxy(phenyl)methyl)-4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carboxylate (compound of Example 22) and TFA (15.7 mg, 0.027 mmol) in DCM (1000 μL, 15.54 mmol) to give a light orange solution. After 1 h, the solvent was evaporated and the residue was purified by flash chromatography to afford Example 23: methyl 2-benzoyl-4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carboxylate (10 mg, 79% yield) as a bright yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27-1.36 (m, 2H) 1.36-1.48 (m, 4H) 1.74-1.88 (m, 2H) 2.14-2.44 (m, 6H) 3.52-3.68 (m, 2H) 3.91 (s, 3H) 7.54 (t, J=7.8 Hz, 2H) 7.69 (t, J=7.4 Hz, 1H) 7.76 (t, J=5.1 Hz, 1H) 7.90 (dd, J=8.2, 1.4 Hz, 1H) 7.94 (d, J=7.0 Hz, 2H) 8.10 (d, J=1.4 Hz, 1H) 8.52 (d, J=8.2 Hz, 1H) 12.43 (s, 1H); HRMS m/z 472.2342 (M+H)+; HPLC 97.1% @ 220 nm and 98.9% @ 254 nm, RT=1.86 minutes.

Provenance & Evidence