8-Chloro-3-methoxy-1,5-naphthyridine → HCID 59843019, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 8-chloro-3-methoxy-1,5-naphthyridine (35 mg, 182 μmol) and 1-(2-aminoethyl)-5-(thiophen-2-yl)pyridin-2(1H)-one (40 mg, 182 μmol) in iPrOH (0.5 mL) was heated to 100° C. overnight. The mixture was partitioned between CH2Cl2 (10 mL) and 1M NaOH (5 mL). The aqueous was further extracted with CH2Cl2 (2×5 mL) and combined organics dried over MgSO4 then purified on silica (12 g) eluting with 15-60% of 5% (MeOH/CH2Cl2). MS (ESI pos. ion) m/z (MH+): 379. Calc'd exact mass for C20H18N4O2S: 378. 1H NMR (400 MHz, Chloroform-d) 8 ppm 3.09 (br. s., 1H) 3.85 (q, J=6.13 Hz, 2H) 3.93 (s, 3H) 4.28 (t, J=5.97 Hz, 2H) 6.57 (d, J=5.48 Hz, 1H) 6.65 (d, J=9.59 Hz, 1H) 6.81 (d, J=2.74 Hz, 1H) 6.91-7.00 (m, 2H) 7.10-7.15 (m, 1H) 7.34 (d, J=2.54 Hz, 1H) 7.50-7.58 (m, 2H) 8.40 (d, J=2.74 Hz, 1H) 8.45 (d, J=5.48 Hz, 1H).

Provenance & Evidence