Ammonium Chloride → HCID 178424148, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of EXAMPLE 581D (232 mg) in N,N-dimethylamide (10 ml) was added NaN3 (281 mg) and NH4Cl (231 mg). The mixture was stirred at reflux overnight. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (200 ml) and water (60 ml). The organic phase was washed with brine and dried over Na2SO4. Concentration of the solvent gave crude product which was dissolved in dichloromethane/trifluoroacetic acid (1:1, 4 ml) and heated to 125° C. in a microwave (CEM Discover) for 20 minutes. The mixture was concentrated and the residue was dissolved in dimethylsulfoxide/methanol (1/1, 2 ml) and loaded on HPLC for purification. 1H NMR (300 MHz, DMSO-d6) δ 10.63 (m, 1H), 8.26 (m, 1H), 7.86 (m, 1H), 7.74 (d, 1H), 7.53 (m, 2H), 7.42 (m, 5H), 7.33 (m, 2H), 7.11 (m, 3H), 6.90 (d, 1H), 4.23 (t, 2H), 2.29 (m, 2H), 2.13 (s, 3H).

Provenance & Evidence