Phenylacetic Acid → HCID 67161348, compound

Participants

Reaction Steps

To a 4 mL vial was added the product from Example 11B (20 mg in DMA), phenylacetic acid [1.5 equivalents in dimethyl acetamide, O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 2 equivalents in dimethyl acetamide) and triethylamine (3 equivalents, neat). The vial was capped and microwaved at 150° C. for 30 minutes. The reaction was checked by LC/MS and concentrated to dryness upon completion. The residue was dissolved in 1:1 MeOH:DMSO and purified by reverse phase HPLC [Phenomenex Luna C8(2) 5 um 100 Å AXIA column (30 mm×75 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/min [0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A]. 1H NMR (500 MHz, DMSO-d6) δ ppm 11.89-11.91 (bs, 1H), 8.43 (dd, J=8.0, 1.3 Hz, 1H), 8.12-8.15 (m, 1H), 7.96-8.08 (m, 2H), 7.32-7.42 (m, 4H), 7.26-7.30 (m, 1H), 3.73 (s, 2H); MS (ESI+) M/Z 348 (M+H)+, 365 (M+NH4)+.

Provenance & Evidence