Diisopropylethylamine → HCID 11234462, compound

Participants

Reaction Steps

Following the same procedure in Example 3, Step A, using isoxazolidine hydrochoride (29.5 mg, 0.26 mmol), diisopropylethylamine (144 μL, 106.6 mg, 0.83 mmol) and a solution of 1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazole-5-carboxylic acid (82.1 mg, 0.25 mmol) (for preparation, see in Example 4, Step E) in DMF (5 mL) at 0° C., and later, HATU (114.0 mg, 0.30 mmol). The mixture was stirred for 4 h at room temperature, and quenched by adding H2O (5 mL). Upon evapoartion, the desired title compound was purified by reversed-phase HPLC (C-18 column) using 20-50% CH3CN/H2O to give 94.8 mg (76%) of a white solid. 1H NMR (400 MHz, CD3OD): δ 0.86 (t, J=7.42 Hz, 3 H), 1.27 (m, 5 H), 1.66 (m, 3 H), 1.69 (s, 6 H), 1.79 (m, 2 H), 2.04 (q, J=7.49 Hz, 2 H), 2.13 (m, 1 H), 2.43 (m, 2 H), 3.94 (m, 2 H), 4.07 (t, J=6.74 Hz, 2 H), 4.50 (d, J=7.62 Hz, 2 H), 8.00 (m, 2 H), 8.19 (s, 1 H). MS (ESI) (M+H)+=384.2. Anal. Calcd for C23H33N3O2+1.40 TFA+1.30 H2O (566.59): C, 54.69; H, 6.58; N, 7.42. Found: C, 54.66; H, 6.50; N, 7.68.

Provenance & Evidence