N'-(7-bromoquinoxalin-2-yl)-4-(2-cyanopropan-2-yl)benzohydrazide → 2-(4-(8-Bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl) phenyl)-2-methylpropanenitrile

HRID 711377Notes

Reaction equation

HRID 711377 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][NH:13][C:14](=O)[C:15]3[CH:20]=[CH:19][C:18]([C:21]([C:24]#[N:25])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1>CC(O)=O.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]3[N:9]2[C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:23])([CH3:22])[C:24]#[N:25])=[CH:17][CH:16]=2)=[N:13][N:12]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66803266N'-(7-bromoquinoxalin-2-yl)-4-(2-cyanopropan-2-yl)benzohydrazide

Product 1

HCID 668033032-(4-(8-Bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl) phenyl)-2-methylpropanenitrileYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of N′-(7-bromoquinoxalin-2-yl)-4-(2-cyanopropan-2-yl)benzohydrazide (2.2 g, 0.054 mol) in 3 mL of AcOH was stirred at 100° C. overnight. After cooling to room temperature, the reaction mixture was diluted with water (5 mL). The solid was collected on a filter, and washed with Sat. NaHCO3 (5 mL) to give 2-(4-(8-bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl) phenyl)-2-methylpropanenitrile as a yellow solid (1.8 g, yield 85.0%). MS (m/z): 392 (M+H)+.

Workup

  1. customThe solid was collected on a filter
  2. washwashed with Sat. NaHCO3 (5 mL)

Sources & evidence

ORD record
ord-738486baa82c485b8a6b9581cab5a20f
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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