Реакция #2286351

Уравнение реакции

(2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

(2-Cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

sodium acetate

→

2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile

Выход 51.3%

2-[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile

Выход 51.3%

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was cooled to 25° C.
2. 2
   workup.ADDITIONwas then poured onto water (125 mL)
3. 3
   ЭкстракцияThe resulting orange mixture was extracted with ethyl acetate (150 mL)
4. 4
   ПромывкаThe combined organics were washed with a saturated aqueous sodium chloride solution
5. 5
   Сушкаdried with magnesium sulfate
6. 6
   workup.ADDITIONtreated with Norite neutral decolorizing carbon
7. 7
   Фильтрацияfiltered through celite
8. 8
   Промывкаwashed with ethyl acetate
9. 9
   КонцентрированиеThe filtrate was concentrated under vacuum
10. 10
    ДругоеPurification by HPLC (10-90 acetonitrile/water with 0.1% trifluoroacetic acid over 30 min)

Методика

A solution of (2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (95) (190 mg, 0.38 mmol) in glacial acetic acid (4 mL) was treated with sodium acetate (158 mg, 1.15 mmol). The resulting mixture was heated to 120° C. for 3.5 h. The reaction was cooled to 25° C. and was then poured onto water (125 mL). The resulting orange mixture was extracted with ethyl acetate (150 mL). The combined organics were washed with a saturated aqueous sodium chloride solution, dried with magnesium sulfate, treated with Norite neutral decolorizing carbon, filtered through celite and washed with ethyl acetate. The filtrate was concentrated under vacuum. Purification by HPLC (10-90 acetonitrile/water with 0.1% trifluoroacetic acid over 30 min) afforded 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (96) (87.2 mg, 44%) as an off-white solid; ES-HRMS m/e calcd for C19H16Cl2N6O3 (M+H)+ 447.0734, found 447.0735. Exact Mass=446.0661; Molecular Weight=447.2838.

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