Oxane-4-carboxylic acid → HCID 58575079, compound

HRID 1396653Notes

Reaction equation

HRID 1396653 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.[O:19]1[CH2:24][CH2:23][CH:22]([C:25](O)=[O:26])[CH2:21][CH2:20]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.ClCCl.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([NH:17][NH:18][C:25]([CH:22]2[CH2:23][CH2:24][O:19][CH2:20][CH2:21]2)=[O:26])=[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

Participants

8

Reactant 4

HCID 219302Oxane-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 86660662Methyl 3-chloro-2-hydrazino7-methylquinoxaline-6-carboxylate

Product 1

HCID 58575079HCID 58575079, compoundYield 64.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 10 g of methyl 3-chloro-2-hydrazino-7-methylquinoxaline-6-carboxylate, 5.9 g of tetrahydro-2H-pyran-4-carboxylic acid, 16 mL of triethylamine, and 100 mL of dichloromethane was added 21 g of bromo(tripyrrolidin-1-yl)phosphonium hexafluorophosphate, followed by stirring at room temperature for 9 hours. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution and chloroform. The solid was collected by filtration and washed with ethyl acetate to obtain 9.1 g of methyl 3-chloro-7-methyl-2-[2-(tetrahydro-2H-pyran-4-ylcarbonyl)hydrazino]quinoxaline-6-carboxylate as a pink solid. Further, to the filtrate obtained above was added chloroform, and then the aqueous layer was separated. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was washed with ethyl acetate to obtain 3.58 g of methyl 3-chloro-7-methyl-2-[2-(tetrahydro-2H-pyran-4-ylcarbonyl)hydrazino]quinoxaline-6-carboxylate as a colorless solid.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-36d5283fa38146f480eaf0fe33df2a02
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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