Реакция #87775

Уравнение реакции

tert-butyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate

6-chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate

TFA

→

pure product

Выход 7.1%

N-(4-Chloro-3-(1-(3,4-di chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)pivalamide

Выход 7.1%

Растворители

DCM

DCM

Условия реакции

Обработка

1. 1
   workup.STIRRINGfurther stirred for 20 h at room temperature
2. 2
   ДругоеThe reaction mass was quenched in water
3. 3
   Экстракцияextracted with DCM
4. 4
   Концентрированиеconcentrated
5. 5
   Другоеto afford crude product which
6. 6
   Другоеwas purified by column chromatography
7. 7
   Промывкаeluting with MeOH

Методика

To a solution of tert-butyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate (Intermediate-52, 0.060 g, 0.21 mmol) in DCM (10 mL) was added solution of 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate (Intermediate-51, 0.101 g, 0.32 mmol) in DCM and the reaction mixture was stirred for 20 h at room temperature, followed by addition of TFA (3 mL) and further stirred for 20 h at room temperature. The reaction mass was quenched in water, extracted with DCM and concentrated to afford crude product which was purified by column chromatography eluting with MeOH:DCM to afford 0.007 g of pure product. 1H NMR (300 MHz, CDCl3): δ 1.20 (s, 9H), 4.44 (d, J=5.4 Hz, 2H), 6.20 (m, 1H), 7.29 (m, 1H), 7.41-7.49 (m, 2H), 7.91 (d, J=8.1 Hz, 1H), 8.15 (s, 1H); MS (m/z): 471.26 (M+).

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