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

HRID 1853138Notes

Reaction equation

HRID 1853138 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 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 ambient temperature 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 ambient temperature for 18 hours
  2. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-3d5f0e54f50143218e3b9ed7520e90ce
Source dataset
uspto-grants-2015_02
Patent number
US08962631B2

Reaction notes

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