Aniline → HCID 10384320, compound

Participants

Reaction Steps

A solution of EXAMPLE 11A (50 mg), hydroxyazobenzotriazole (20 mg), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (50 mg), diisopropylethylamine (0.025 mL), N,N-dimethylaminopyridine (100 mg), and dimethylacetamide (2 mL) was stirred for 30 minutes, treated with aniline (12.6 mg), stirred for 18 hours, treated with trisamine resin (0.26 g), stirred for 2 hours, treated with carbonate resin (0.090 g), stirred for 2 hours, and filtered. The filtrate was concentrated, and the concentrate was dissolved in dichloromethane, applied to a silica gel-containing solid-phase extraction cartridge, and eluted with 25% ethyl acetate/hexanes then 10% methanol/dichloromethane. The product was dissolved in trifluoroacetic acid, stirred at 80° C. for 18 hours in a sealed vial, and concentrated. This concentrate was dissolved in methanol, treated with anion exchange resin, and filtered. The filtrate was concentrated, and the concentrate was purified by reverse phase HPLC. NMR (300 MHz, CD3OD) δ 8.65 (s, 1H), 8.05 (m, 1H), 7.60-7.70 (m, 2H), 7.30-7.40 (m, 2H), 7.10-7.15 (m, 1H), 3.85-4.15 (m, 5H), 2.40-2.55 (m, 1H), 2.10-2.50 (m, 1H).

Provenance & Evidence