Water → Ethyl ({5-bromo-3-[(2-chloro-3,6-difluorobenzyl)amino]pyrazin-2-yl}amino)(oxo)acetate

HRID 80536

Reaktionsgleichung

Reaktionsgleichung von HRID 80536
[Br:1][C:2]1[N:3]=[C:4]([NH:9][CH2:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=2[Cl:19])[C:5]([NH2:8])=[N:6][CH:7]=1.C(N(C(C)C)CC)C.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[O:30].O>C(Cl)Cl>[Br:1][C:2]1[N:3]=[C:4]([NH:9][CH2:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=2[Cl:19])[C:5]([NH:8][C:29](=[O:30])[C:28]([O:32][CH2:33][CH3:34])=[O:31])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 70211Ethyl oxoacetateHCID 521913N,N-Diethyl-2-propanamineHCID 866594195-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamine

Produkt 1

HCID 86659420Ethyl ({5-bromo-3-[(2-chloro-3,6-difluorobenzyl)amino]pyrazin-2-yl}amino)(oxo)acetateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamine (5.15 mmol, 1.8 g) and N,N-diethylisopropylamine (9.30 mmol, 2 mL) in CH2Cl2 (20 mL) was added ethyl glyoxylate (5.41 mmol, 0.74 g) at 0° C. The suspension was warmed up naturally and stirred overnight. Water was added to dissolve the precipitation. The combined organic layers from extraction were combined, dried, concentrated, and then subjected to a silica gel column chromatography by using CH2Cl2/MeOH (9:1) as eluents, furnishing ethyl ({5-bromo-3-[(2-chloro-3,6-difluorobenzyl)amino]pyrazin-2-yl}amino)(oxo)acetate in 52% yield (1.20 g).

Aufarbeitung

  1. temperatureThe suspension was warmed up naturally and
  2. dissolutionto dissolve
  3. customthe precipitation
  4. extractionThe combined organic layers from extraction
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-800182b303a74dc8b2921d8b57c7ff7c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846664B2

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