Tert-butyl 4-(2-(7-bromoquinoxalin-2-yl)hydrazinecarbonyl)piperidine-1-carboxylate → 8-Bromo-1-(piperidin-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline

HRID 711380Notes

Reaction equation

HRID 711380 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]([CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=O)=[N:9]2)=[CH:4][CH:3]=1>CC(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]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[N:13][N:12]=3)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 66803410Tert-butyl 4-(2-(7-bromoquinoxalin-2-yl)hydrazinecarbonyl)piperidine-1-carboxylate

Product 1

HCID 668032678-Bromo-1-(piperidin-4-yl)[1,2,4]triazolo[4,3-a]quinoxalineYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of tert-butyl 4-(2-(7-bromoquinoxalin-2-yl)hydrazinecarbonyl)piperidine-1-carboxylate (900 mg, 2.0 mmol) in AcOH (10 mL) was refluxed overnight. Then the solvent was removed, and the residue was purified by ISCO (MeOH/H2O=20%-90%) to afford 8-bromo-1-(piperidin-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline as a pale yellow solid (550 mg, yield 83.0%). MS (m/z): 332 (M+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. customThen the solvent was removed
  3. customthe residue was purified by ISCO (MeOH/H2O=20%-90%)

Sources & evidence

ORD record
ord-08daaeac9458446798f911c1381b3226
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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