Hydrochloride methanol → HCID 23449075, compound

A 110% hydrochloric acid/methanol solution (1 ml) and 120 mg of 10%Pd—C were added to a solution of 0.44 g of 7-azidoacetylimidazo[5,1-b]thiazole in 50 ml of methanol and 50 ml of THF. The atmosphere in the reactor was replaced with hydrogen. The system was stirred at room temperature for 2 hr. The reaction mixture was filtered. The solvent was removed by distillation. To the residue were added 10 ml of DMF, 0.39 g of 4-nitrophenyl formate, and 0.66 ml of triethylamine. The mixture was stirred at room temperature for 30 min. Dichloromethane was added to the reaction solution. The mixture was washed with water and saturated brine in that order, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=10:1) to give 0.24 g of 7-formylaminoacetylimidazo[5,1-b]thiazole.

1. filtrationThe reaction mixture was filtered
2. customThe solvent was removed by distillation
3. additionTo the residue were added 10 ml of DMF, 0.39 g of 4-nitrophenyl formate, and 0.66 ml of triethylamine
4. stirringThe mixture was stirred at room temperature for 30 min
5. additionDichloromethane was added to the reaction solution
6. washThe mixture was washed with water and saturated brine in that order
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe solvent was removed by distillation
9. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=10:1)

ORD record

ord-d2c971caddcb4fe6948e1b1747b21c7d

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677331B2