Sodium Acetate → 1-acetyl-8-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-3-hydroxy-5-methyl-1,5-dihydro-4H-pyrrolo[3,2-c]-1,8-naphthyridin-4-one

HRID 13820Notes

Reaction equation

HRID 13820 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6](=[O:35])[N:7]([CH3:34])[C:8]2[C:13]([C:14]=1[NH:15][C:16](=[O:18])[CH3:17])=[CH:12][C:11]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[C:10]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])[N:9]=2)=[O:4].CC([O-])=O.[Na+]>CN(C=O)C.O.CCOC(C)=O>[C:16]([N:15]1[C:14]2[C:13]3[CH:12]=[C:11]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)[C:10]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=4[Cl:33])=[N:9][C:8]=3[N:7]([CH3:34])[C:6](=[O:35])[C:5]=2[C:3]([OH:4])=[CH:2]1)(=[O:18])[CH3:17]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 86610501N-[3-(bromoacetyl)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

Product 1

HCID 114891461-acetyl-8-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-3-hydroxy-5-methyl-1,5-dihydro-4H-pyrrolo[3,2-c]-1,8-naphthyridin-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of Step A (25 mg) was added NaOAc (60 mg) in DMF (2.5 mL) and water (0.3 mL) at room temperature. The reaction stirred overnight and was diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine. The concentrated residue was purified by flash chromatography on silica gel with a gradient elution of 0-100% EtOAc in hexane affording the title compound. HPLC/MS: 512.0 (M+1), 514.0 (M+3); Rt=4.18 min.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customThe concentrated residue was purified by flash chromatography on silica gel with a gradient elution of 0-100% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-6c7674da996d44448724e655e8bb211a
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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