1-Hydroxybenzotriazole → HCID 73057537, compound

Participants

Reaction Steps

(S)-3-(2-(1-amino-7-oxononyl)oxazol-5-yl)-1-methylquinolin-2(1 H)-one (1 eq), prepared as described in steps 1 to 5 of Example 7, was treated with a solution of thiazole-5-carboxylic acid (1.3 eq), HOBT (1.3 eq) and EDC.HCl (1.3 eq) in DMF (premixed for 3 min), followed by DIPEA (1.3 eq). The mixture was stirred at room temperature for 2 h and the desired product was isolated by preparative RP-HPLC, using water (+0.01% TFA) and MeCN (+0.01% TFA) as eluents (column C18). The pooled product fractions were lyophilized and the product was obtained as a white solid. MS (ES) C26H28N4O4S requires: 492.59, found: 493. 1H-NMR (400 MHz, DMSO-d6) δ: 9.28 (1 H, d, J=8 Hz), 9.26 (1 H, s), 8.62 (1 H, s), 8.29 (1 H, s), 7.91 (1 H, d, J=7.6 Hz), 7.84 (1 H, s), 7.68 (1 H, t, J=7.2 Hz), 7.61 (1 H, d, J=8.2 Hz), 7.34 (1 H, t, J=7.6 Hz), 5.27-5.22 (1 H, m), 3.75 (3 H, s), 2.39-2.36 (4 H, m), 2.09-2.06 (1 H, m), 2.00-1.96 (1H, m), 1.50-1.27 (6 H, m), 0.89 (3 H, t, J=7.2 Hz).

Provenance & Evidence