Phosphoric Acid → HCID 19605170, compound

A 0.081 ml potion of dry methanol was added dropwise to 0.35 ml of a dry dichloromethane solution containing 0.175 ml of chlorosulfonyl isocyanate at a bath temperature of -55° C. under stirring, and the mixture was then stirred for 20 minutes. Then, the precipitate was dissolved in 2.0 ml of dry dichloromethane, and this mixed solution was added dropwise to 10 ml of a dry dichloromethane solution containing 153 mg of 3-aminomethylimidazo[5,1-b]thiazole and 0.28 ml of triethylamine at an internal temperature of -47° C. over 2 minutes, and the mixture was then stirred at -47 to -35° C. for 60 minutes. After the addition of 10 ml of a 1/15M phosphoric acid buffer, the solution was adjusted to pH 7.5 with 5% sodium bicarbonate, and after salting-out, extraction was carried out five times with 30 ml of dichloromethane. Further, the aqueous layer was adjusted to pH 6 with 1N hydrochloric acid, and extraction was then carried out five times with 30 ml of ethyl acetate. The extract was combined with the above dichloromethane extract. Afterward, the solution was dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The resulting residue was recrystallized from methanol to obtain 87.4 mg of the title compound as a light yellow crystal.

1. stirringthe mixture was then stirred for 20 minutes
2. stirringthe mixture was then stirred at -47 to -35° C. for 60 minutes
3. extractionextraction
4. extractionFurther, the aqueous layer was adjusted to pH 6 with 1N hydrochloric acid, and extraction
5. extractionextract
6. dry with materialAfterward, the solution was dried over anhydrous magnesium sulfate
7. customthe solvent was then evaporated under reduced pressure
8. customThe resulting residue was recrystallized from methanol

ORD record

ord-749b2e9d1702432fa907b91ea1351e62

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05990101