Trifluoroacetic acid → HCID 178444052, compound

Participants

Reaction Steps

To a stirring solution of tert-butyl 2-(N-((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate INT-49 (40 mg, 0.055 mmol) in DCM (2 mL) was added TFA (1 mL). After stirring at room temperature for 2 h, the solvents were concentrated and the residue purified by preparative HPLC to afford 15 mg (40%) of 2-(N-((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetic acid 366 as a white powder. LCMS-ESI (m/z) calculated for C40H44N4O6: 676; found 677 [M+H]+, tR=6.77 min (Method 4). 1H NMR (400 MHz, DMSO) 12.82 (br s, 1H), 12.21 (br s, 1H), 10.29 (s, 1H), 7.65 (d, J=8.2 Hz, 2H), 7.30-7.57 (m, 4H), 7.27-7.15 (m, 4H), 7.15-6.92 (m, 1H), 6.89-6.75 (m, 4H), 4.71 (s, 1H), 4.62 (s, 1H), 4.08 (s, 2H), 3.91 (m, 3H), 3.81-3.69 (m, 4H), 3.57 (s, 2H), 1.73-1.61 (m, 2H), 1.43-1.20 (m, 8H), 0.90-0.80 (m, 3H).

Provenance & Evidence