Diisopropylethylamine → Methyl 1-((3-amino-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate

Participants

Reaction Steps

A slurry of methyl 1-((3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate (0.390 g, 0.78 mmol) and 10% palladium on carbon, 50% water, (0.41 g) and N,N-diisopropylethylamine (0.27 mL, 1.6 mmol) was treated with a hydrogen balloon and stirred rapidly for 2 h, then was flushed with nitrogen, filtered through celite, rinsing with MeOH/DCM. The filtrate was concentrated in vacuo and the residue purified by silica gel chromatography 40 g, 20-100% EA/hexanes to give methyl 1-((3-amino-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate as a yellow solid. MS (ESI) m/z: Calculated: 470.2; Observed: 470.8 (M++1).

Provenance & Evidence