Tetrahydrofuran → HCID 58574949, compound

HRID 1189459Notes

Reaction equation

HRID 1189459 reaction equation
C[O:2][C:3]1[C:12]([NH:13][NH:14][C:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=O)=[N:11][C:10]2[C:5](=[CH:6][C:7]([CH3:27])=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]=2)[N:4]=1.O1CCCC1.S(Cl)(Cl)=O>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:27][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][C:8]=1[C:23]([O:25][CH3:26])=[O:24])[N:11]1[C:15]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:14][N:13]=[C:12]1[C:3](=[O:2])[NH:4]2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 67133866HCID 67133866, compound

Product 1

HCID 58574949HCID 58574949, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a mixed liquid of 4.83 g of methyl 2-methoxy-7-methyl-3-[2-(tetrahydro-2H-pyran-4-ylcarbonyl)hydrazino]quinoxaline-6-carboxylate and 96.6 mL of tetrahydrofuran were added 2 drops of N,N-dimethylformamide and 1.90 mL of thionyl chloride at room temperature, followed by stirring at 70° C. overnight. The reaction liquid was diluted with chloroform and added to ice-water portionwise, followed by stirring for 10 minutes. The obtained solid was collected by filtration and washed with diethyl ether to obtain 1.94 g of methyl 7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxylate as a pale yellow solid.

Workup

  1. customThe reaction liquid
  2. stirringby stirring for 10 minutes
  3. filtrationThe obtained solid was collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-79d2ce644eee4f6f86864c451fb3e769
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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