Hydrochloric Acid → HCID 78160390, compound

Temperature

0 °C

To a solution of tert-butyl (1-((9-bromo-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (0.045 g, 0.094 mmol) in dichloromethane (4 mL) cooled to 0° C. was added hydrogen chloride, 2M in diethyl ether (6 mL, 0.094 mmol) slowly over a period of 5 min. The reaction mixture was stirred at 0° C. for 5 min, then at room temperature for 2 h. The solvents were removed by concentration under reduced pressure. The crude product was taken up in water (10 mL) and washed with diethyl ether (3×10 mL). The aqueous layer was concentrated and purified by reverse phase HPLC (0.1% TFA in water and acetonitrile) to yield 1-((9-bromo-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-amine (0.016 g, 0.042 mmol, 45% yield) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 8.68 (bs, 2H), 8.35 (s, 1H), 8.26 (s, 1H), 6.90 (s, 1H), 5.39 (s, 2H), 4.41 (m, 1H), 4.27 (m, 1H), 3.76 (m, 1H), 1.82 (m, 2H), 1.69 (m, 1H), 1.05 (m, 6H). LCMS (ESI) m/e 377.0 [(M+H)+, calcd for C18H22BrN2O2 377.1]; LC/MS retention time (Method D): tR=1.25 min; HPLC retention time (method A): tR=8.59 min; HPLC retention time (method B): tR=10.33 min.

1. waitat room temperature for 2 h
2. customThe solvents were removed by concentration under reduced pressure
3. washwashed with diethyl ether (3×10 mL)
4. concentrationThe aqueous layer was concentrated
5. custompurified by reverse phase HPLC (0.1% TFA in water and acetonitrile)

ORD record

ord-bc2923f0149d444683cec5f4312e4809

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969564B2