Aniline → 3-amino-6-bromo-N-phenylpyrazine-2-carboxamide

HRID 78557

Reaktionsgleichung

Reaktionsgleichung von HRID 78557
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CCN(C(C)C)C(C)C.[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C1C=CN=CC=1)C.CS(C)=O.O>[NH2:1][C:2]1[C:3]([C:9]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Komponenten

8

Edukt 4

HCID 6115AnilineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Produkt 1

HCID 529371483-amino-6-bromo-N-phenylpyrazine-2-carboxamideAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (3.5 g, 16.05 mmol), 1,1′-carbonyldiimidazole (5.205 g, 32.10 mmol), DIPEA (2.282 g, 3.075 mL, 17.66 mmol) and DMAP (98.04 mg, 0.8025 mmol) were combined in DMSO (131.2 mL) and stirred for 30 min. Aniline (1.495 g, 1.463 mL, 16.05 mmol) was then added and the resulting solution stirred at RT for 18 hours. After this time water was added and the product collected by filtration to give a brown powder (3.5 g, 74% Yield).

Aufarbeitung

  1. stirringthe resulting solution stirred at RT for 18 hours
  2. filtrationthe product collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5fed8c8601554ad38411a17b244187ee
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

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