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Acetic Acid → methyl 4-chloro-8-methyl-1-(tetrahydro-2H-thiopyran-4-ylmethyl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate

HRID 1807842
Notes
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Reaction equation

HRID 1807842 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][NH2:18])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[CH:6]=2.C(O)(=O)C.[S:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH:30]=O)[CH2:25][CH2:24]1.O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]2[N:4]([C:30]([CH2:29][CH:26]3[CH2:27][CH2:28][S:23][CH2:24][CH2:25]3)=[N:18][N:17]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[CH:6]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 23532962(Tetrahydro-thiopyran-4-YL)-acetaldehydeHCID 86660662Methyl 3-chloro-2-hydrazino7-methylquinoxaline-6-carboxylate

Product 1

HCID 58575435methyl 4-chloro-8-methyl-1-(tetrahydro-2H-thiopyran-4-ylmethyl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylateYield 29.2%

Reagents, catalysts & solvents

1
HCID 6212ChloroformSolvent

Procedure

To a mixed liquid of 1.40 g of methyl 3-chloro-2-hydrazino-7-methylquinoxaline-6-carboxylate and 28.0 mL of acetic acid was added 820 mg of tetrahydro-2H-thiopyran-4-ylacetaldehyde, followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and to the residue was added 28.0 mL of N,N-dimethylformamide, followed by replacement with argon. Then, a mixed liquid of 706 mg of copper(II) chloride and 28.0 mL of N,N-dimethylformamide was added thereto, followed by stirring at 50° C. for 20 minutes and at 100° C. for 1 hour. To the reaction liquid were added water and chloroform, followed by extraction with chloroform, the organic layer was washed with 1 M hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine and, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 600 mg of methyl 4-chloro-8-methyl-1-(tetrahydro-2H-thiopyran-4-ylmethyl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate as a brown solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionto the residue was added 28.0 mL of N,N-dimethylformamide
  3. additionThen, a mixed liquid of 706 mg of copper(II) chloride and 28.0 mL of N,N-dimethylformamide was added
  4. stirringby stirring at 50° C. for 20 minutes and at 100° C. for 1 hour
  5. customTo the reaction liquid
  6. extractionfollowed by extraction with chloroform
  7. washthe organic layer was washed with 1 M hydrochloric acid, water
  8. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine and, dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-19fd2aef05324084a1cfd680856913d4
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08357688B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes