Triethylamine → tert-Butyl 4-((4-(3-(6-methylpyridin-3-yl)ureido)benzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate

To a room temperature solution of tert-butyl 4-((4-aminobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate (5.0 g, 15.1 mmol, 1.0 equiv) and triethylamine (2.1 g, 15.1 mmol, 1.0 equiv) in dry DCM (37 mL) was added 2-methyl-5-isocyanatopyridine (2.22 g, 16.6 mmol, 1.1 equiv) in dry DCM (37 mL) via cannula. After 1 h, the reaction mixture was filtered and washed with water (25 mL) and brine (25 mL). The solution was dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel purification (5% MeOH/95% EtOAc—15% MeOH/85% EtOAc) provided the title compound as a white foam (7.03 g, 100%). LCMS [M+H]+=467.2.

1. filtrationthe reaction mixture was filtered
2. washwashed with water (25 mL) and brine (25 mL)
3. dry with materialThe solution was dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customSilica gel purification (5% MeOH/95% EtOAc—15% MeOH/85% EtOAc)

ORD record

ord-2bc9b1d91be945c48bdeeb0cc42ebf8d

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653081B2