Hydrochloric Acid → 2-{4-Amino-2-[(3-chloro-4-methoxy-5-methylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}-N-methylacetamide hydrochloride

Temperature

25 °C

Ethanol (100.5 ml) and water (3.975 ml) were added to 2-{4-amino-2-[(3-chloro-4-methoxy-5-methylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}-N-methylacetamide (3.00 g, 6.40 mmol), and the resulting mixture was then stirred at 25° C. Thereafter, a water-ethanol solution (3.28 ml, 1.92 mmol) of 0.585 M hydrogen chloride that had been prepared by diluting concentrated hydrochloric acid (1.0 ml) with ethanol (19.0 ml) was added to the reaction mixture. A seed crystal (0.3 mg) was added to the mixture at the same temperature as described above, and a water-ethanol solution (6.56 ml, 3.84 mmol) of 0.585 M hydrogen chloride was added dropwise to the resulting mixture over 2 hours. The mixture was stirred for 30 minutes. Thereafter, concentrated hydrochloric acid (0.695 ml, 8.34 mmol) was added dropwise to the reaction mixture over 1 hour, and the resulting mixture was then stirred for 1 hour. The precipitated crystal was filtrated, was then washed with ethanol (15 ml), and was then dried under reduced pressure at 40° C. for 14 hours, so as to obtain the above title compound (2.89 g, 5.96 mmol). Yield: 93%.

1. additionwas added to the reaction mixture
2. additionwas added dropwise to the resulting mixture over 2 hours
3. stirringThe mixture was stirred for 30 minutes
4. stirringthe resulting mixture was then stirred for 1 hour
5. filtrationThe precipitated crystal was filtrated
6. washwas then washed with ethanol (15 ml)
7. customwas then dried under reduced pressure at 40° C. for 14 hours

ORD record

ord-4081eae955a246efaf3fb16cf3abaae7

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815880B2