Hydrochloric Acid → 8-methyl-4-oxo-1-(tetrahydro-2H-thiopyran-4-ylmethyl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid

HRID 1189445Notes

Reaction equation

HRID 1189445 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:17]([CH2:20][CH:21]3[CH2:26][CH2:25][S:24][CH2:23][CH2:22]3)=[N:18][N:19]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14]C)=[O:13])=[C:7]([CH3:16])[CH:6]=2.[O:27]1CCCC1.[OH-].[Na+].Cl>CO>[CH3:16][C:7]1[CH:6]=[C:5]2[C:10]([NH:11][C:2](=[O:27])[C:3]3[N:4]2[C:17]([CH2:20][CH:21]2[CH2:26][CH2:25][S:24][CH2:23][CH2:22]2)=[N:18][N:19]=3)=[CH:9][C:8]=1[C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58575435methyl 4-chloro-8-methyl-1-(tetrahydro-2H-thiopyran-4-ylmethyl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate

Product 1

HCID 585756078-methyl-4-oxo-1-(tetrahydro-2H-thiopyran-4-ylmethyl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixed liquid of 1.70 g of methyl 4-chloro-8-methyl-1-(tetrahydro-2H-thiopyran-4-ylmethyl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate, 18.0 mL of tetrahydrofuran, and 18.0 mL of methanol was added 9.20 mL of a 3 M aqueous sodium hydroxide solution, followed by stirring at 60° C. overnight. 3 M hydrochloric acid was added thereto to adjust the pH to about 3, and the precipitated solid was collected by filtration and dried under reduced pressure to obtain 1.20 g of 8-methyl-4-oxo-1-(tetrahydro-2H-thiopyran-4-ylmethyl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid as a yellow solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-ad9c48c9dbc0486fbf5b1ca1679d958d
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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