Ammonium Chloride → (S)-9-methylthio-5-[3-(2H-tetrazol-5-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one

Participants

Reaction Conditions

Reaction Steps

(S)-5-(3-Cyanophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (366 mg, 1.04 mol) obtained in Step 1 of Example 71 was dissolved in DMF (7 mL), and the mixture was stirred at 100° C. for 9.5 hours after adding ammonium chloride (222 mg, 4.16 mmol) and sodium azide (176 mg, 2.71 mmol). The mixture was extracted by addition of ethyl acetate and water. The aqueous layer was collected, and the pH was adjusted to 5 with 1 mol/L hydrochloric acid. After extraction with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and reslurried with diethyl ether to give (S)-9-methylthio-5-[3-(2H-tetrazol-5-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (293 mg, 71%).

Provenance & Evidence