Lithium Hydroxide → HCID 9911639, compound

Participants

Reaction Steps

1.0 N LiOH (0.44 mL, 0.44 mmole) was added to a solution of methyl (±)-8-[3-(2-pyridylamino)-1-propyloxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (159.5 mg, 0.34 mmole) in THF (1.7 mL) and H2O (1.3 mL) at RT. The yellow, cloudy reaction became homogeneous within 10 min. After 24 hr, the reaction was concentrated to dryness and the yellow residue was dissolved in H2O (4 mL). The solution was filtered, then was carefully neutralized (pH≈7) with 1.0 N HCl. The precipitate was collected, washed with plenty of H2O, and dried in high vacuum at 40-45° C. to afford the title compound (130.0 mg, 83%) as an off-white solid: HPLC (PRP-1®, 25% CH3CN/H2O containing 0.1% TFA) k′=3.1; 1H NMR (400 MHz, DMSO-d6) δ 7.91-8.00 (m, 1 H), 7.28-7.40 (m, 1 H), 7.02 (d, J=9.2 Hz, 1 H), 6.76-6.87 (m, 2 H), 6.51-6.02 (m, 1 H), 6.39-6.50 (m, 2 H), 5.30 (d, J=16.6 Hz, 1 H), 4.10-4.30 (m, 3 H), 4.02(t, J=6.3 Hz, 1 H), 3.70-3.82 (m, 1 H), 3.20-3.45 (m, 2 H, partially obscured by residual solvent signal), 2.99 (dd, 1 H), 2.59-2.74 (m, 2 H), 2.39 (dd, J=16.9, 4.8 Hz, 1 H), 1.90-2.03 (m, 2 H); MS (ES) m/e 452 (M+H)+. Anal. Calcd for C22H24F3N3O4.0.5 H2O: C, 57.39; H. 5.47; N, 9.13. Found: C, 57.39; H, 5.18; N, 9.00.

Provenance & Evidence