Quinoline → HCID 10237225, compound

Participants

Reaction Steps

A mixture of Example 14D (40 mg, 0.11 mmol), 5% Pd/BaSO4 (8.1 mg) and quinoline (8.1 μL) in methanol (3 mL) was stirred under hydrogen (20 psi) at room temperature for 12 minutes and filtered. The filtrate was concentrated and the residual oil was purified by HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA to provide the desired product (30 mg, 75%). MS (APCI) m/e 369 (M−H)−; 1H NMR (300 MHz, CD3OD) δ 8.57 (d, J=6.8 Hz, 2H), 8.29 (d, J=2.4 Hz, 1H), 8.04 (s, 1H), 7.69 (d, J=6.4 Hz, 2H), 7.57 (d, J=7.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 7.33 (t, J=1.7 Hz, 1H), 7.21 (s, 1H), 7.14 (m, 2H), 7.02 (td, J=8.1, 1.0 Hz, 1H), 6.95 (d, J=12.2 Hz, 1H), 4.24 (dd, J=10.5, 3.0 Hz, 1H), 4.08 (dd, J=10.5, 5.6 Hz, 1H), 3.92 (m, 1H), 3.26 (m, 2H); Anal. Calcd for C23H22N4O. 3.6 TFA: C, 46.45; H, 3.30; N, 7.17. Found: C, 46.56; H, 3.35; N, 7.34.

Provenance & Evidence