Hydrochloric Acid → HCID 57855913, compound

HRID 2039601Notes

Reaction equation

HRID 2039601 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[NH:15]C(OC(C)(C)C)=O)[N:11]=[CH:10][CH:9]=[N:8]2)=[O:4].Cl>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[NH2:15])[N:11]=[CH:10][CH:9]=[N:8]2)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57855964HCID 57855964, compound

Product 1

HCID 57855913HCID 57855913, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

7.1 g (24.0 mmol) 7-tert-butoxycarbonylamino-quinoxaline-6-carboxylic acid methyl ester is added to 50 ml dioxane and 110 ml HCl 6N and heated at a temperature of 50° C. The dioxane phase is evaporated and the residue is diluted with 150 ml water. The water phase is neutralized with NaOH 2N (˜pH 8), saturated with NaCl and extracted with ethyl acetate and THF. After evaporation of the solvent, the residue is submitted to flash-chromatography to give 2.2 g (41%) of the title compound. m.p.: 180-182° C.

Workup

  1. customThe dioxane phase is evaporated
  2. additionthe residue is diluted with 150 ml water
  3. extractionextracted with ethyl acetate and THF
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-2d48ef7a2ab54cffaa5c18df35e78528
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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