Cyclopropanecarboxylic acid → N'-(7-bromoquinoxalin-2-yl)cyclopropanecarbohydrazide

HRID 711366Notes

Reaction equation

HRID 711366 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][NH2:13])=[N:9]2)=[CH:4][CH:3]=1.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.[CH:47]1([C:50](O)=[O:51])[CH2:49][CH2:48]1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][NH:13][C:50]([CH:47]3[CH2:49][CH2:48]3)=[O:51])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 52002657-Bromo-2-hydrazinylquinoxalineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 66803436N'-(7-bromoquinoxalin-2-yl)cyclopropanecarbohydrazide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 7-bromo-2-hydrazinylquinoxaline (200 mg, 0.83 mmol) in DMF (3 mL) was added HATU (380 mg, 1 mmol), DIPEA (0.205 mL, 1 mmol) and cyclopropanecarboxylic acid (71 mg, 0.83 mmol). After stirring at r.t. for 5 h, the mixture was diluted with EtOAc. The organic layer was washed with water for three times, then concentrated to afford N′-(7-bromoquinoxalin-2-yl)cyclopropane-carbohydrazide as yellow solid which was used directly in the next step. m/z 309 (M+H)+.

Workup

  1. washThe organic layer was washed with water for three times
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4404a10cb1fb4730b7ea7712e16e4625
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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