Hydrochloric Acid → HCID 66727899, compound

Temperature

120 °C

A mixture of 4-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)aniline (70 mg) and 2-chlorobenzo[d]oxazole (57 mg) in 1-methylpyrrolidinone (2 mL) was stirred at 120° C. for 30 min. After this time, the reaction was cooled to room temperature, diluted with AcOEt (50 mL), washed with saturated NaHCO3 aqueous solution (50 mL), water (2×50 mL) then brine (50 mL), dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (CH2Cl2 to 1:19 MeOH/CH2Cl2), dissolved in 1,4-dioxane (2 ml), treated with 4 M HCl in 1,4-dioxane (0.500 mL, 2.00 mmol) and concentrated under reduced pressure. The residue obtained was triturated with boiling is CH3CN to give the title compound (60 mg).

1. temperatureAfter this time, the reaction was cooled to room temperature
2. washwashed with saturated NaHCO3 aqueous solution (50 mL), water (2×50 mL)
3. dry with materialbrine (50 mL), dried over Na2SO4
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe residue obtained
7. customwas purified by silica gel column chromatography (CH2Cl2 to 1:19 MeOH/CH2Cl2)
8. dissolutiondissolved in 1,4-dioxane (2 ml)
9. concentrationconcentrated under reduced pressure
10. customThe residue obtained
11. customwas triturated with boiling

ORD record

ord-edfc902896d844938e2eeed2fb5adfad

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029536B2