1-Hydroxybenzotriazole → ETHYL N-[4-({3-CYCLOHEXYL-5-[4-(TRIFLUOROMETHOXY)PHENYL]-1H-PYRAZOL-1-YL}METHYL)BENZOYL]-beta-ALANINATE

Participants

Reaction Steps

A solution of 66.7 mg product from Step A Example 6, 34.5 mg EDC, 24.3 mg HOBt in 0.5 mL DMF was stirred at room temperature for 30 minutes. DIEA (31 μL) and β-amino-alanine ethyl ester hydrochloride (27.6 mg) were added and the mixture stirred for additional 16 hours. The solvent was removed under reduced pressure. The title compound was isolated as a white solid by preparative HPLC using 60˜80% MeCN gradient over 10 minutes at 8.0 mL per minute with 0.1% TFA on a 9.4×250 mm SB-C18 Zorbax column followed by lyophilization. 1H NMR (CD3OD, 600 MHz) δ 7.68 (d, J=8.4 Hz, 2H), 7.39˜7.42 (m, 2H), 7.28 (d, J=8.1 Hz, 2H), 6.99 (d, J=8.3 Hz, 2H), 6.31 (s, 1H), 5.37 (s, 2H), 4.11 (q, J=7.1 Hz, 2H), 3.59 (t, J=6.8 Hz, 2H), 2.66 (tt, J=11.6 & 3.5 Hz, 1H), 2.61 (t, J=6.8 Hz, 2H), 1.96˜2.00 (m, 2H), 1.80˜1.84 (m, 2H), 1.71˜1.75 (m, 1H), 1.45˜1.52 (m, 2H), 1.37˜1.45 (m, 2H), 1.25˜1.33 (m, 1H), 1.21 (t, J=7.1 Hz, 3H). LC-MS: 2.44 min. (M+H=544.4).

Provenance & Evidence