Ethanolamine → HCID 67168446, compound

Participants

Reaction Steps

To 2-hydroxy-2-(2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)acetic acid (Preparation 84C, isomer 1, 0.033 g, 0.070 mmol) in DMF (1 mL) were sequentially added N-methylmorpholine (0.031 mL, 0.279 mmol), 2-aminoethanol (5.48 μl, 0.091 mmol) and HATU (0.040 g, 0.105 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with 0.5 mL of MeOH and subjected to preparative. HPLC (Waters Xbridge C18 19×100 mm; solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA). The desired fractions were collected, concentrated and freeze dried using MeOH (0.3 mL) and water (0.7 mL) to yield 2-hydroxy-N-(2-hydroxyethyl)-2-(2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)acetamide (0.013 g, 0.024 mmol, 34.3% yield) as a pale yellow solid. The compound had an HPLC retention time=3.54 min. (condition C); LC/MS M+1=516; 1H NMR (500 MHz, CDCl3) δ ppm 7.65 (2H, d, J=6.9 Hz), 7.48-7.58 (3H, m), 7.33-7.44 (3H, m), 6.72 (1H, br. s.), 5.12 (1H, s), 3.76 (2H, t, J=4.9 Hz), 3.46-3.53 (2H, m), 3.12-3.25 (4H, m).

Provenance & Evidence