تفاعل #1180997

معادلة التفاعل

EDCI.HCl

DIPEA

[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid

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

HOBt

→

5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide

المردود 58.7%

المذيبات

water

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued at ambient temperature overnight
4. 4
   استخلاصextracted with ethylacetate
5. 5
   غسيلwashed with brine
6. 6
   تركيزconcentrated

الإجراء التجريبي

DIPEA (154 mg, 1.2 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (100 mg, 0.4 mmol) in DMF (2.0 mL) followed by HOBt (60 mg, 0.49 mmol) and EDCI.HCl (93 mg, 0.49 mmol). After 2 minutes of stirring, 4-(2-trifluoromethyl-phenoxy)-piperidine trifluoroacetate (167 mg, 0.49 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethylacetate, washed with brine and concentrated to afford 111 mg (57.81% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 473.17, 97.38%, 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 8.1 (bs, 1H), 7.9-7.3 (m, 8H), 7.2-7.0 (m, 2H), 4.9 (bs, 1H), 4.2 (m, 2H), 3.8-2.9 (m, 4H), 2.0-1.7 (m, 3H).

المصدر