Ammonium Chloride → HCID 178442322, compound

Participants

Reaction Conditions

Reaction Steps

1-(Benzo[d][1,3]dioxol-5-yl)-N-(2-(4-cyano-2-methylbutan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide (83 mg, 0.20 mmol) was dissolved in N,N-dimethylformamide (1 mL) containing ammonium chloride (128 mg, 2.41 mmol), sodium azide (156 mg, 2.40 mmol), and a magnetic stir bar. The reaction mixture was heated at 110° C. for 40 minutes in a microwave reactor. The crude product was filtered and then purified by preparative HPLC using a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-(2-methyl-4-(1H-tetrazol-5-yl)butan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide. ESI-MS m/z calc. 458.2, found 459.2(M+1)+. Retention time of 1.53 minutes. NMR (400 MHz, CD3CN) 9.23(s, 1H), 7.51-7.48(m, 2H), 7.19(d, J=8.6 Hz, 1H), 7.06-7.03(m, 2H), 6.95-6.89(m, 2H), 6.17(dd, J=0.7, 2.2 Hz, 1H), 6.02(s, 2H), 2.61-2.57(m, 2H), 2.07-2.03(m, 2H), 1.55-1.51(m, 2H), 1.39(s, 6H), 1.12-1.09(m, 2H).

Provenance & Evidence