4-Toluenesulfonyl chloride → HCID 67052431, compound

mCPBA (2.33 g, 13.5 mmol) was added to a suspension of tert-butyl 3-(2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propylcarbamate (4.86 g, 9.67 mmol) in chloroform (50 mL). The reaction mixture was allowed to stir for 4 hours, then concentrated ammonium hydroxide (27 mL) and p-toluenesulfonyl chloride (2.03 g, 10.6 mmol) were added. The reaction mixture was allowed to stir overnight at room temperature, then was filtered. The filtrate was diluted with saturated aqueous sodium bicarbonate (50 mL) and extracted with chloroform (2×40 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford a brown solid that was purified by chromatography using a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform) to afford 1.00 g of tert-butyl 3-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl}propylcarbamate as a yellow solid that contained some minor impurities.

1. stirringto stir overnight at room temperature
2. filtrationwas filtered
3. additionThe filtrate was diluted with saturated aqueous sodium bicarbonate (50 mL)
4. extractionextracted with chloroform (2×40 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto afford a brown solid that
9. customwas purified by chromatography
10. washa HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform)

ORD record

ord-126ebde67349422693cffff05729ce38

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897767B2