4-Fluoroaniline → HCID 67347151, compound

Participants

Reaction Steps

Prepared from 3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 1, Step B; 130 mg, 0.50 mmol) and 1-((4-fluorophenyl)carbamoyl) -cyclopropanecarboxylic acid (123 mg, 0.550 mmol; prepared from cyclopropane-1,1-dicarboxylic acid and 4-fluoroaniline using the methods described in WO 2005/030140 and by Shih and Rankin, Synth. Comm. 1996, 26(4), 833-836) according to the procedure described for Example 10. The crude was purified by preparative TLC (10% MeOH/CH2Cl2). The product was obtained as a waxy solid (60 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 10.06 (s, 1H), 8.51 (s, 1H), 8.29 (s, 1H), 7.75 (m, 2H), 7.56 (d, J=5 Hz, 1H), 7.45 (m, 2H), 7.26 (m, 2H), 7.06 (m, 2H), 6.51 (d, J=5 Hz, 1H), 1.80 (m, 2H), 1.62 (m, 2H). LRMS (ESI pos) m/e 466 (M+1). HPLC: 97% purity (220 nm).

Provenance & Evidence