N,N-Diethyl-2-propanamine → 5-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamine

HRID 80535

Reaktionsgleichung

Reaktionsgleichung von HRID 80535
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[Cl:10][C:11]1[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:12]=1[CH2:13][NH2:14].C(N(C(C)C)CC)C>CCCCO>[Br:9][C:5]1[N:6]=[C:7]([NH:14][CH2:13][C:12]2[C:15]([F:20])=[CH:16][CH:17]=[C:18]([F:19])[C:11]=2[Cl:10])[C:2]([NH2:1])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 521913N,N-Diethyl-2-propanamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 27735452-Chloro-3,6-difluorobenzylamine

Produkt 1

HCID 866594195-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A solution of 2-amino-3,5-dibromopyrazine (29 mmol, 7.35 g), 2-chloro-3,6-difluorobenzylamine (29 mmol, 5.16 g), and N, N-diethylisopropylamine (32 mmol, 5.6 mL) in n-BuOH (20 mL) was refluxed for 72 hrs. After volatile components were removed on rotavap, EtOAc and water were added to the residue to facilitate the extraction. The combined organic layers were combined, dried, concentrated, and then subjected to a silica gel column chromatography by using hexanes/EtOAc (4:1) as eluents, furnishing 5-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamine in 70% yield (7.14 g).

Aufarbeitung

  1. customAfter volatile components were removed on rotavap
  2. additionEtOAc and water were added to the residue
  3. extractionthe extraction
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d71052b2363c431a8a193624a3f04fd1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846664B2

Verknüpfte Notizen

Wird geladen…