Diisopropylethylamine → HCID 59553212, compound

Participants

Reaction Steps

A mixture of 4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-ylamine (1.38 g, 5.07 mmol), 2-chloroisonicotinoyl chloride (1.34 g, 7.6 mmol), DIPEA (1.81 ml, 10.1 mmol) and THF (30 ml) is stirred at room temperature for 12 hours. The mixture is quenched with water (100 ml). The crude product is extracted with EtOAc (2×50 ml), the combined organic layers are dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash column chromatography (3% MeOH in EtOAc) to afford 2-chloro-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-isonicotinamide (1.07 g, 51%). 1H NMR (DMSO-d6) δ 10.61 (s, 1H), 8.62 (d, 1H), 8.21 (d, 1H), 8.10 (s, 1H), 7.95 (m, 2 H), 7.59 (d, 2 H), 7.49 (d, 1H), 7.09 (d, 1H), 4.33 (m, 2 H), 3.61 (m, 4 H), 2.92 (m, 2 H), 2.61 (m, 4 H). MS: 412 (M+1).

Provenance & Evidence