Ammonium Chloride → HCID 178428378, compound

Participants

Reaction Conditions

Reaction Steps

5-[2-Chloro-6-methyl-4-(1H-tetrazol-5-ylamino)-phenoxy]-N-cyclopropyl-2-hydroxy-benzenesulfon-amide was prepared from 5-[2-chloro-4-cyanoamino-6-methyl-phenoxy]-N-cyclopropyl-2-hydroxy-benzenesulfonamide according to a procedure analogous to that described in EXAMPLE 1, Step C. Sodium azide (1.2 equiv) and ammonium chloride (10 equiv) were used, and the reaction was heated to 165° C. for 3 hours. After the reaction had been acidified, the aqueous mixture was washed with ethyl acetate (3×10 ml). The combined organic extracts were extracted with aqueous 1N HCl (3×50 ml), and brine (50 ml). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (methanol:water:dichloromethane 25:3:72) to afford the title product of Example 5. MS (APCI+) Calc.: 436.1, Found: 436.9 (M+1).

Provenance & Evidence