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1-Hydroxybenzotriazole → 7-[(4-methyl-3-phenyl piperazin-1-yl)carbonyl]-1-propyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one

HRID 1189479
Notes
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Reaction equation

HRID 1189479 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=O)[CH:9]=2)[N:4]2[C:15]([CH2:18][CH2:19][CH3:20])=[N:16][N:17]=[C:3]12.Cl.Cl.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH:25]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>[Cl-].[Na+].O.CN(C)C=O.C(N(CC)CC)C>[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:12]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]2[C:15]([CH2:18][CH2:19][CH3:20])=[N:16][N:17]=[C:3]2[C:2](=[O:1])[NH:11]3)=[O:14])[CH2:26][CH:25]1[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 450750971-Methyl-2-phenylpiperazine dihydrochlorideHCID 585752814-Oxo-1-propyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid

Product 1

HCID 58575568
7-[(4-methyl-3-phenyl piperazin-1-yl)carbonyl]-1-propyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one
Yield 83.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 150 mg of 4-oxo-1-propyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid, 165 mg of 1-methyl-2-phenyl piperazine dihydrochloride, 0.24 mL of triethylamine, 112 mg of 1-hydroxybenzotriazole, and 2.25 mL of N,N-dimethylformamide was added 158 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, followed by stirring at room temperature for 1 day. To the reaction liquid were added a saturated aqueous sodium hydrogen carbonate solution and saturated brine, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform/methanol=95/5 to 90/10). The obtained solid was triturated with a mixture of ethanol and diisopropyl ether to give a powder. The precipitate was collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to obtain 197 mg of 7-[(4-methyl-3-phenyl piperazin-1-yl)carbonyl]-1-propyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one as a white powder.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=95/5 to 90/10)
  6. customThe obtained solid was triturated with a mixture of ethanol and diisopropyl ether
  7. customto give a powder
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with diisopropyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-9951c495fbfa4da7a780cba5a35ecc66
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08674096B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes