Potassium Phosphate, Tribasic → HCID 89784660, compound

Participants

Reaction Conditions

Reaction Steps

Prepared similarly to that described in Example 254 using 2-(3-chloro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 254c; 47 mg, 0.150 mmol), (R)-1,1,1-trifluoropropan-2-amine hydrochloride (44.9 mg, 0.301 mmol, SynQuest Laboratories, Alachua, Fla.), Pd(tBu3P)2 (Strem, Newburyport, Mass.; 7.68 mg, 0.015 mmol), and K3PO4 (128 mg, 0.601 mmol), heating at 100° C. for 18 h. Purification by silica gel (100% DCM to 4% 2 M NH3 in MeOH/DCM) then by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) provided (R)-2-(2-methyl-3-((1,1,1-trifluoropropan-2-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (10% yield). MS (ESI, pos. ion) m/z: 390.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 1.61 (br. s., 3H) 2.66 (s, 3H) 2.96 (t, J=6.85 Hz, 2H) 3.66 (td, J=6.90, 2.45 Hz, 2H) 4.81 (s, 1H) 4.91 (dq, J=14.04, 6.93 Hz, 1H) 5.29 (br. s., 1H) 7.12 (d, J=2.15 Hz, 1H) 7.48 (t, J=7.82 Hz, 1H) 7.73 (d, J=7.04 Hz, 1H) 7.95 (dd, J=7.63, 1.17 Hz 1H) 11.59 (br. s., 1H). 19F NMR (376 MHz, DMSO-d6) δ ppm −76.30 (3F, s).

Provenance & Evidence