تفاعل #45236

معادلة التفاعل

solution

3-[3-(5-amino-3-t-butyl-pyrazol-1-yl)-phenyl]-propionic acid ethyl ester

4-methoxy-phenylamine

CDI

→

3-(3-{3-t-butyl-5-[3-(4-methoxy-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester

المردود 45.2%

المذيبات

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting mixture was stirred at RT overnight
2. 2
   أخرىthen quenched with of water (50 mL)
3. 3
   استخلاصThe reaction mixture was extracted with ethyl acetate (3×50 mL)
4. 4
   غسيلthe combined organic extracts were washed with brine
5. 5
   تجفيفdried (NaSO4)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced presume
8. 8
   أخرىto yield a residue which
9. 9
   أخرىwas purified by flash chromatography

الإجراء التجريبي

A mixture of 4-methoxy-phenylamine (123 mg, 1.0 mmol) and CDI (165 mg, 1.0 mmol) in DMF (2 mL) was stirred at RT for 30 min, and was then added a solution of Example Z (315 mg, 1.0 mmol) in DMF (2 mL). The resulting mixture was stirred at RT overnight then quenched with of water (50 mL). The reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic extracts were washed with brine, dried (NaSO4), filtered, concentrated under reduced presume to yield a residue which was purified by flash chromatography to afford 3-(3-{3-t-butyl-5-[3-(4-methoxy-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester (210 mg, 45%). 1H-NMR (CD3OD): 7.46 (t, J=7.6 Hz, 1H), 7.38 (s, 1H), 7.34 (d, J=7.6 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 6.38 (s, 1H), 4.09 (q, J=7.2 Hz, 2H), 3.75 (s, 3H), 3.00 (t, J=7.6 Hz, 2H), 2.68 (t, J=7.6 Hz, 2H), 1.33 (s, 9H), 1.20 (t, J=7.6 Hz, 3H); MS (ESI) m/z: 465 (M+H+).

المصدر