Diisopropylethylamine → N'-(7-bromoquinoxalin-2-yl)-4-(2-cyanopropan-2-yl)benzohydrazide

HRID 711376Notes

Reaction equation

HRID 711376 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.[C:14]([C:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)([CH3:18])[CH3:17])#[N:15].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>CN(C=O)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:23](=[O:24])[C:22]3[CH:21]=[CH:20][C:19]([C:16]([C:14]#[N:15])([CH3:17])[CH3:18])=[CH:27][CH:26]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 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)HCID 146986034-(1-Cyano-1-methylethyl)benzoic acid

Product 1

HCID 66803266N'-(7-bromoquinoxalin-2-yl)-4-(2-cyanopropan-2-yl)benzohydrazideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-bromo-2-hydrazinylquinoxaline (1.5 g, 0.063 mol) and 4-(2-cyanopropan-2-yl) benzoic acid (1.1 g, 0.063 mol) in DMF (5 mL) was added HATU (2.4 g, 0.063 mol) and DIEA (1.2 g, 0.095 mol). The reaction mixture was then stirred at r.t. overnight. The solution was diluted with water (5 mL), and the solid was collected on a filter to give N′-(7-bromoquinoxalin-2-yl)-4-(2-cyanopropan-2-yl)benzohydrazide as a yellow solid (2.2 g, yield 85.0%). MS (m/z): 412 (M+H)+.

Workup

  1. customthe solid was collected on
  2. filtrationa filter

Sources & evidence

ORD record
ord-cf179ae7294f49369d8bd300fccac34b
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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