Реакция #45236

Уравнение реакции

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

Выход 45.2%

Растворители

DMF

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe resulting mixture was stirred at RT overnight
2. 2
   Другоеthen quenched with of water (50 mL)
3. 3
   ЭкстракцияThe reaction mixture was extracted with ethyl acetate (3×50 mL)
4. 4
   Промывкаthe combined organic extracts were washed with brine
5. 5
   Сушкаdried (NaSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under reduced presume
8. 8
   Другоеto yield a residue which
9. 9
   Другоеwas purified by flash chromatography

Методика

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+).

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