Diisopropylethylamine → N-(1,3-Thiazol-2-yl)pyridin-2-amine 21

Participants

Reaction Steps

2-{[4-(Chloromethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (180 mg, 0.72 mmole) and 1-glycoloylpiperazine hydrochloride (259 mg, 1.44 mmole) were combined in DMSO (2 mL). To this was added diisopropylethylamine (0.38 mL, 2.15 mmole) at RT. After 3 hr the mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 5-15% EtOH/EtOAc then 5-10% MeOH/CHCl3) gave the title compound as a pale yellow solid: 1H NMR (d6-DMSO) δ12.19 (s, 1 H), 8.33 (d, 1 H, J=5.1 Hz), 8.32 (s, 1 H), 7.14 (s, 1 H), 7.0 (d, 1 H, J=5.2 Hz), 4.54 (t, 1 H, J=5.6 Hz), 4.08 (d, 2 H, J=5.6 Hz), 3.55 (s, 2 H), 3.49 (s, 2 H), 3.36 (s, 2 H), 2.38 (s, 4 H); MS [M+H]+=359.1285.

Provenance & Evidence