Thionyl Chloride → methyl 4-chloro-8-methyl-1-(tetrahydro-2H-pyran-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate

HRID 1396654Notes

Reaction equation

HRID 1396654 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][NH:18][C:19]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=O)=[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.S(Cl)(Cl)=O>O1CCCC1>[Cl:1][C:2]1[C:3]2[N:4]([C:19]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]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

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58575079HCID 58575079, compound

Product 1

HCID 58575100methyl 4-chloro-8-methyl-1-(tetrahydro-2H-pyran-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 12.7 g of methyl 3-chloro-7-methyl-2-[2-(tetrahydro-2H-pyran-4-ylcarbonyl)hydrazino]quinoxaline-6-carboxylate and 250 mL of tetrahydrofuran was added 5 mL of thionyl chloride, followed by stirring at 70° C. overnight. After cooling to room temperature, the solvent was evaporated under reduced pressure and the obtained solid was washed with diethyl ether to obtain 10.4 g of methyl 4-chloro-8-methyl-1-(tetrahydro-2H-pyran-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate as a pale yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. washthe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-df6d62e2d7ff4bab97a54ce0d0af8480
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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