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

HRID 2204778Notes

Reaction equation

HRID 2204778 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-fff54a70b89947c69e9f997d829ddbbb
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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