Tetrahydrofuran → HCID 59736811, compound

Participants

Reaction Steps

To a solution of acid 4 (scheme 1) (125 mg, 0.439 mmol) in DMF (3 mL) was added BOP (293 mg, 0.662 mmol). After stirring this solution for 10 minutes, aniline 311 (197 mg, 0.659 mmol) was added, along with triethylamine (0.31 mL, 2.22 mmol). The resulting solution was stirred at room temperature for 16 h prior to removal of the solvent, and dissolution of the residue in THF (5 mL). A solution of TBAF in THF (1.0 M, 0.66 mL, 0.659 mmol) was then added, and the reaction mixture was stirred at room temperature for 5 minutes, diluted with a saturated solution of NaCl (10 mL), and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated. After purification by flash chromatography (eluent 0-80% EtOAc in hexanes), the title compound 312 was obtained as a light yellow solid (82 mg, 41% yield). 1H NMR: (DMSO) δ (ppm): 3.62 (s, 3H), 3.69 (s, 3H), 4.34 (d, J=5.7 Hz, 2H), 6.03 (m, 2H), 6.35 (d, J=2.2 Hz, 1H), 6.68 (d, J=8.4 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 7.32 (t, J=7.2 Hz, 1H), 7.37 (dd, J=10.4, 1.6 Hz, 1H), 7.45 (t, J=7.6 Hz, 2H), 7.52 (d, J=8.0 Hz, 2H), 7.59 (d, J=7.6 Hz, 2H), 7.95 (d, J=8.0 Hz, 2H), 8.03 (br s. 1H), 9.58 (br s, 1H), 10.00 (br s, 1H). MS: (calc.) 454.5; (obt.) 455.4 (MH)+.

Provenance & Evidence