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

HRID 1959346Notes

Reaction equation

HRID 1959346 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 529371483-amino-6-bromo-N-phenylpyrazine-2-carboxamideYield 74.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-876a0d56c82e44628c1eee5fdaf1b967
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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