Potassium Phosphate, Tribasic → HCID 71731272, 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; 23 mg, 0.074 mmol), 1-(trifluoromethyl)cyclopropanamine hydrochloride (47.5 mg, 0.294 mmol, Astatech, Inc., Bristol, Pa.), Pd(tBu3P)2 (Strem, Newburyport, Mass.; 3.76 mg, 7.35 μmol), and K3PO4 (94 mg, 0.441 mmol), heating at 120° C. for 16 h. Purification by silica gel (100% DCM to 3% 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 2-(2-methyl-3-((1-(trifluoromethyl)cyclopropyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (14% yield). MS (ESI, pos. ion) m/z: 402.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 1.29-1.33 (m, 2H) 1.58-1.62 (m, 2H) 2.62 (s, 3H) 2.95 (t, J=6.85 Hz, 2H) 3.66 (td, J=6.85, 2.54 Hz, 2H) 5.31 (br. s., 1H) 5.45 (s, 1H) 7.17 (d, J=2.15 Hz, 1H) 7.48 (t, J=7.63, 1 H) 7.71 (dd, J=8.12, 1.27 Hz, 1H) 7.99 (dd, J=7.53, 1.27 Hz, 1H) 12.47 (br. s., 1H). 19F NMR (376 MHz, DMSO-d6) δ ppm −72.08 (3F, s).

Provenance & Evidence