Water → HCID 131728169, compound

HRID 15311Notes

Reaction equation

HRID 15311 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[N:17]=2)[N:12]=[CH:11][C:10]=1[F:21])C(OC)=O.[Cl-].[Li+].O.C(OCC)(=O)C>CS(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[N:17]=2)[N:12]=[CH:11][C:10]=1[F:21]

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 68684268Dimethyl[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanedioate

Product 1

HCID 131728169HCID 131728169, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of dimethyl[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanedioate (52 g, 169 mmol), lithium chloride (14.5 g, 340 mmol) and water (3.43 ml, 190 mmol) in DMSO (1175 ml) was heated at 100° C. for 24 hours and cooled. The solution was shaken with water and ethyl acetate, separated and the organic phase washed twice with water. The total aqueous was re-extracted with ethyl acetate and this water-washed. The combined organic phase was dried and evaporated and the residue chromatographed, using a hexane/ethyl acetate gradient, to give the desired product containing about 10% of starting material (35.79 g).

Workup

  1. temperaturecooled
  2. customseparated
  3. washthe organic phase washed twice with water
  4. extractionThe total aqueous was re-extracted with ethyl acetate
  5. washthis water-washed
  6. customThe combined organic phase was dried
  7. customevaporated
  8. customthe residue chromatographed

Sources & evidence

ORD record
ord-96383d4113704fa5824ad9656debf080
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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