Acetic Acid → HCID 59645218, compound

HRID 2252810Notes

Reaction equation

HRID 2252810 reaction equation
C[O-].[Na+].[CH3:4][N:5]([S:31]([CH3:34])(=[O:33])=[O:32])[C:6]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[C:13]([O:20]S(C2C=CC(C)=CC=2)(=O)=O)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2.C(O)(=O)C>CO.CN(C=O)C>[OH:20][C:13]1[C:14]([C:16]([O:18][CH3:19])=[O:17])=[N:15][C:6]([N:5]([CH3:4])[S:31]([CH3:34])(=[O:33])=[O:32])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 59645219HCID 59645219, compound

Product 1

HCID 59645218HCID 59645218, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of sodium methoxide (122 mg, 2.26 mmol) in dry methanol (5 mL) was added to methyl 5-[methyl(methylsulfonyl)amino]-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate (420 mg, 0.90 mmol) dissolved in a minimum amount of DMF and the resulting solution was heated to 50° C. for one hour. The reaction was cooled, glacial acetic acid (104 μL, 1.80 mmol) was added and the reaction was concentrated to dryness in vacuo. The resulting residue was triturated with ethanol and the solids were collected by vacuum filtration to give the desired product as a yellow solid.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationthe reaction was concentrated to dryness in vacuo
  3. customThe resulting residue was triturated with ethanol
  4. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-e4592d567a44461094bd47f626655921
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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