تفاعل #1181040

معادلة التفاعل

HOBt

4-(2-trifluoromethyl-phenoxy)-piperidine trifluoroacetate

DIPEA

[(1-Phenyl-1H-imidazole-4-carbonyl)-amino]-acetic acid

EDCI

→

1-phenyl-1H-imidazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide

المردود 58.2%

المذيبات

water

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting mixture was stirred at ambient temperature overnight
2. 2
   ترشيحthe precipitate was filtered
3. 3
   أخرىThe precipitate was purified by recrystallisation from a mixture of 20% EtOAc in hexane (15 mL) and MeOH (0.1 mL)

الإجراء التجريبي

DIPEA (236 mg, 1.826 mmol) was added to a stirred solution of [(1-Phenyl-1H-imidazole-4-carbonyl)-amino]-acetic acid (prepared from Intermediate 68 by means of Step 3 of the General Scheme) (100 mg, 0.4 mmol) in DMF (5 mL) followed by HOBt (60.5 mg, 0.4 mmol) and EDCI (195 mg, 1.02 mmol). After 2 minutes of stirring, 4-(2-trifluoromethyl-phenoxy)-piperidine trifluoroacetate (126 mg, 0.45 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water, and the precipitate was filtered. The precipitate was purified by recrystallisation from a mixture of 20% EtOAc in hexane (15 mL) and MeOH (0.1 mL) to afford 113 mg (58.2% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 473, 96.85%. 1H NMR (300 MHz, DMSO-d6): δ 8.4 (s, 1H), 8.3 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.68-7.6 (t, 2H), 7.6 (t, 2H), 7.4-7.34 (m, 2H), 7.14 (t, 1H), 5.0 (m, 1H), 4.2 (d, 2H), 3.7-3.4 (m, 4H), 2.1 (d, 2H), 1.8 (d, 2H).

المصدر