1,2-Dichloroethane → HCID 11384823, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-[3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenoxymethyl]-benzoic acid (100 mg, 0.24 mmol) and methylamine HCl (163 mg, 2.41 mmol) in DMF (1.2 mL) was charged with DIEA (0.42 mL, 2.41 mmol), HOBt (37.0 mg, 0.24 mmol), and EDC (69.0 mg, 0.36 mmol). The brown colored reaction mixture was allowed to stir for 18 h. LC/MS analysis indicated that the reaction was nearly complete. The reaction was heated to 50° C. and allowed to react for an additional 18 h. The DMF was removed in vacuo and the product was chromatographed on silica gel [Jones Flashmaster, 5 g cartridge, eluting with 2% 7N NH3 MeOH:CH2Cl2] to yield the title compound as a pink solid; 1H NMR (CDCl3, 400 MHz) δ 1.99-2.07 (m, 1H), 2.11-2.20 (m, 1H), 2.44-2.50 (m, 2H), 2.57-2.67 (m, 2H), 3.01 (d, J=5.2 Hz, 3H), 3.76-3.85 (m, 1H), 5.17 (s, 2H), 6.99-7.02 (m, 2H), 7.10 (d, J=5.2 Hz, 1H), 7.24-7.27 (m, 2H), 7.37-7.46 (m, 2H), 7.55 (d, J=7.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.85 (s, 1H); MS (ES+): m/z 428.17 (100) [MH+].

Provenance & Evidence