HCID 15471899, compound → 1,6-Naphthyridin-2-amine

A 50% TFA/DCM mixture (10 mL) was added to tert-butyl 1,6-naphthyridin-2-ylcarbamate (2.7 g, 11.0 mmol) from the above step. After 30 minutes, the reaction mixture was concentrated and diluted with 30 mL of water. A saturated NaHCO3 solution (15 mL) was added, and the reaction mixture was extracted twice with 50 mL of EtOAc. The organic layers were combined, concentrated, and purified by chromatography through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient 0-15% MeOH/DCM to give 1,6-naphthyridin-2-amine (1.6 g, 99% yield). MS m/z: 145 (M+1). 1H NMR (400 MHz, (CD3OD)): δ ppm 6.93 (d, J=9.00 Hz, 1H), 7.41 (d, J=6.06 Hz, 1H), 8.05 (d, J=9.00 Hz, 1H), 8.37 (d, J=5.87 Hz, 1H), 8.83 (s, 1H).

1. concentrationthe reaction mixture was concentrated
2. additiondiluted with 30 mL of water
3. additionA saturated NaHCO3 solution (15 mL) was added
4. extractionthe reaction mixture was extracted twice with 50 mL of EtOAc
5. concentrationconcentrated
6. custompurified by chromatography through a Redi-Sep® pre-packed silica gel column (120 g)
7. washeluting with a gradient 0-15% MeOH/DCM

ORD record

ord-6af4072b520d4fc884394d31eb7a5db3

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514566B2