Sodium Hydroxide → HCID 21948170, compound

HRID 2183820Notes

Reaction equation

HRID 2183820 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:34])[CH2:7][S:8][C:9]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]2[C:10]=1[C:11](=[O:33])[CH:12]=[C:13]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[N:14]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C>CCO>[NH:26]([C:13]1[N:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]2[C:10]([C:11](=[O:33])[CH:12]=1)=[C:9]([S:8][CH2:7][C:6]([OH:34])=[O:5])[N:18]=[C:17]([CH3:19])[CH:16]=2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21948185HCID 21948185, compound

Product 1

HCID 21948170HCID 21948170, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous NaOH (2N, 1 mL) was added to a stirred solution of ethyl[(2-anilino-7-methyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridin-5-yl)sulfanyl]acetate (100 mg, 0.23 mmol) in EtOH (8 mL) at room temperature. The mixture was allowed to stir for 4 h and was concentrated in vacuo. The reaction mixture was acidified with 1N HCl and extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification by reverse-phase preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min) provided [(2-anilino-7-methyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridin-5-yl)sulfanyl]acetic acid (56 mg, 60%): LCMS RT: 2.61 min, MH30: 418.2.

Workup

  1. concentrationwas concentrated in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by reverse-phase preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min)

Sources & evidence

ORD record
ord-ea60bbb334b84c198974549a1d932b42
Source dataset
uspto-grants-2005_05
Patent number
US06900205B2

Reaction notes

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