Diisopropylethylamine → HCID 11774312, compound

Participants

Reaction Steps

Following the same procedure in Example 3, Step A, using (4S)-4-methylisoxazolidin-4-ol hydrochoride (36.8 mg, 0.264 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 (83.2 mg, 0.253 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 74.9mg (56%) of a white solid. [a]D: −14.1° (c 0.17,EtOH). 1H NMR (400 MHz, CD3OD): δ 0.85 (t, J=7.52 Hz, 3H), 1.27 (m, 5H), 1.50 (s, 3H), 1.66 (m, 3H), 1.69 (s, 6H), 1.79 (m, 2H), 2.04 (q, J=7.42 Hz, 2H), 2.13 (m, 1H), 3.82 (d, J=11.33 Hz, 1H), 3.89 (d, J=8.40 Hz, 1H), 3.97 (m, 2H), 4.50 (d, J=7.62 Hz, 2H), 7.99.(m, 2H), 8.18 (s, 1H). MS (ESI) (M+H)+=414.2. Anal. Calcd for C24H35N3O3+1.30 TFA+2.00 H2O (597.83): C, 53.44; H, 6.79; N, 7.03. Found: C, 53.39; H, 6.64; N, 7.22.

Provenance & Evidence