Sodium hydride → HCID 178486824, compound

HRID 1859500Notes

Reaction equation

HRID 1859500 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:14]1[CH:23]=[N:22][C:21]2[C:16](=[CH:17][C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[CH:20]=2)[N:15]=1>C1COCC1.CN(C=O)C>[CH3:25][O:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:26][CH3:27])[N:15]=[C:14]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1)[CH:23]=[N:22]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 225731372-Chloro-6,7-dimethoxyquinoxalineHCID 178525780HCID 178525780, compound

Product 1

HCID 178486824HCID 178486824, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A mixture of cis/trans-4-hydroxy-cyclohexanecarboxylic acid (144 mg, 1 mmol) and NaH (60%, 160 mg, 4 mmol) in anhydrous THF/DMF(10 mL/2 mL) is refluxed for one hour before addition of 2-chloro-6,7-dimethoxyquinoxaline (225 mg, 1 mmol). The resulting mixture is continued to refluxed for four hours. The reaction mixture is neutralized to pH 5 and extracted with ethyl acetate (2×50 mL). The combined organic solutions are dried over magnesium sulfate and filtered. The residue after concentration is chromatographed on silica gel (ethyl acetate, followed by methanol) to provide the desired product as a white solid (m.p. 90-93 ° C.). Anal. Calcd. for C17H20N2O5.0.5H2O: C, 59.89; H, 6.19; N, 8.22; Found: C, 59.91; H, 6.62; N, 7.90.

Workup

  1. temperatureto refluxed for four hours
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic solutions are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe residue after concentration
  6. customis chromatographed on silica gel (ethyl acetate, followed by methanol)

Sources & evidence

ORD record
ord-2e7f00202f234ba2aeab40e8efa184c1
Source dataset
uspto-grants-2003_03
Patent number
US06528526B1

Reaction notes

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