Triethylamine → Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetate

HRID 78655

Reaktionsgleichung

Reaktionsgleichung von HRID 78655
[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH2:23])=[O:21])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.CCN(CC)CC.Cl[C:32](=[O:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1COCC1>[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH:23][C:32](=[O:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:21])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:15])=[O:16])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 594716323-Amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide

Produkt 1

HCID 59472330Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetateAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide (2 g, 5.963 mmol) and Et3N (1.810 g, 2.493 mL, 17.89 mmol) were dissolved in THF (128.0 mL) and treated dropwise with ethyl 2-chloro-2-oxo-acetate (814.2 mg, 666.3 μL, 5.963 mmol) at 0° C. The reaction mixture was warmed slowly to room temperature and stirred for 1.5 h. The reaction mixture was filtered and grey solid washed with THF. The filtrate was evaporated to dryness azeotroping with acetonitrile. Then residue was then triturated with acetonitrile to give the product as a yellow solid (1.52 g, 58%); 1H NMR (400 MHZ, DMSO) d 1.19 (m, 6H), 1.32 (m, 3H), 3.34 (m, 1H), 4.32 (m, 2H), 7.88 (m, 2H), 8.56 (m, 2H), 9.07 (s, 1H), 10.95 (s, 1H) and 11.05 (s, 1H) ppm; MS (ES+) 436.32

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washgrey solid washed with THF
  3. customThe filtrate was evaporated to dryness
  4. customazeotroping with acetonitrile
  5. customThen residue was then triturated with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-4b4f714610f449a0801f1607f809f9fe
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

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