Trifluoroacetic acid → HCID 67994756, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-((3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-fluorobenzoic acid, TFA (31.6 mg, 0.048 mmol), N,N-diisopropylamine (0.013 mL, 0.072 mmol), BOP (27.7 mg, 0.063 mmol), and N-methylmorpholine (0.021 mL, 0.188 mmol) in DMF (4 mL) was heated at 45° C. for 1 hr. The mixture was diluted with ethyl acetate (60 mL), washed sequentially with water (3×25 mL) and brine (25 mL), and dried over anhydrous MgSO4. After the solvent was removed under vacuum, the residue was purified by reverse phase HPLC. The correct fraction was concentrated under vacuum, basified with saturated NaHCO3 solution, and extracted with ethyl acetate (3×30 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (13.3 mg, 0.025 mmol, 51.0% yield) as a yellow solid. LCMS (M+H)+=525.09. 1H NMR (500 MHz, DMSO-d6) δ: 11.72 (s, 1H), 8.37 (s, 1H), 8.25 (s, 1H), 7.82-7.79 (m, 2H), 7.72 (d, J=7.8 Hz, 1H), 7.65 (m, 1H), 7.63-7.58 (m, 2H), 7.50 (d, J=6.9 Hz, 1H), 7.41 (d, J=2.2 Hz, 1H), 7.20 (d, J=8.6 Hz, 1H), 6.76 (dd, J1=8.9 Hz, J2=2.2 Hz, 1H), 5.08 (d, J=17.2 Hz, 1H), 4.98 (d, J=17.2 Hz, 1H), 4.21 (m, 2H), 3.77 (m, 2H), 3.40 (s, 3H), 1.92 (s, 3H).

Provenance & Evidence