Hydrochloric Acid → HCID 86591950, compound

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Reaction Steps

To the MeOH solution, 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.73 g, 8.4 mmol) was added and stirred at 75° C. After 8 days, AcOH (15 mL) was added and stirred at 80° C. overnight. Additional 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.73 g, 8.4 mmol) was added then stirred at 80° C. overnight. After cooling, the mixture was poured into NaHCO3 (aq). Formed precipitate was collected by filtration, washed with ethyl acetate then dried under reduced pressure to give methyl (5-(4-acetoamidophenoxy)-3,4-diazaindolin-2-yl)carbamate (983.0 mg, 41%). To a solution of methyl (5-(4-acetoamidophenoxy)-3,4-diazaindolin-2-yl)carbamate (102.4 mg, 0.3 mmol) in water (3 mL) was added 2N HCl (aq) (3.0 mL) then refluxed for 1 hr and stirred at room temperature for 1 hr. The mixture was extracted with ethyl acetate. The organic layer was washed with NH4OH (aq), dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (33.6 mg, 37%): MS m/e 342 (M+1).

Provenance & Evidence