1-Butanol → HCID 178463607, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-[5-fluoro-8-(3-fluorophenyl)cinnolin-7-yl]ethanamine (73 mg, 0.26 mmol) [from peak 1 of Examples 20 and 21, step B] and 2-amino-6-bromopurine (82 mg, 0.38 mmol) in 1-butanol (0.51 mL, 5.6 mmol) was treated with N,N-diisopropylethylamine (67 μL, 0.38 mmol), degassed with nitrogen for 5 minutes and stirred at 120° C. for 18 hours. The reaction mixture was diluted with methanol (10 mL), stirred and filtered. The filtrate was purified first by RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 60 mL/minute) and then by RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/minute) to give the desired product in 26%. LCMS for C21H17F2N8 (M+H)+: m/z=419.2; Found: 418.9. 1H NMR (300 MHz, DMSO-d6): δ 12.1 (br s, 1H), 9.44 (d, J=5.9 Hz, 1H), 8.25-8.22 (m, 1H), 8.13-8.01 (m, 1H), 7.94-7.83 (m, 1H), 7.72-7.53 (m, 3H), 7.40-7.29 (m, 1H), 7.28-7.22 (m, 1H), 5.45-5.21 (m, 3H), 1.42-1.38 (m, 3H).

Provenance & Evidence