2-Methyl-5-Nitroaniline → N-(2-methyl-5-nitrophenyl)thieno[2,3-b]pyrazine-6-carboxamide

HRID 1184885Notes

Reaction equation

HRID 1184885 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:2]=12.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:46][C:47]1[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][C:48]=1[NH2:49]>CN(C=O)C>[CH3:46][C:47]1[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][C:48]=1[NH:49][C:10]([C:8]1[S:7][C:3]2=[N:4][CH:5]=[CH:6][N:1]=[C:2]2[CH:9]=1)=[O:12]

Participants

6

Reactant 4

HCID 74442-Methyl-5-NitroanilineHCID 81531DiisopropylethylamineHCID 7164578Thieno[2,3-b]pyrazine-6-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67125678N-(2-methyl-5-nitrophenyl)thieno[2,3-b]pyrazine-6-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of thieno[2,3-b]pyrazine-6-carboxylic acid (250 mg, 1.387 mmol), HATU (633 mg, 1.665 mmol) and DIPEA (0.459 mL, 2.77 mmol) in DMF (5 mL) was stirred for 15 min. 2-methyl-5-nitroaniline (211 mg, 1.387 mmol) was added and stirred at 60° C. for 4 h. Quenched in citric acid solution and the resulting precipitate was collected to give N-(2-methyl-5-nitrophenyl)thieno[2,3-b]pyrazine-6-carboxamide 75 (400 mg, 92%). (m/z)=315 (M+H)+.

Workup

  1. customQuenched in citric acid solution
  2. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-4f7cadb7f3794f9da829cd6bef1f9b05
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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