Cesium carbonate → N-(3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)-2-hydroxyacetamide

HRID 13819Notes

Reaction equation

HRID 13819 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[N:14][C:15]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH:17]=2)[N:12]([CH3:34])[C:11](=[O:35])[C:10]=1[C:36](=[O:38])[CH3:37])=[O:7])(=O)C.C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl.CO.CCOC(C)=O>[C:36]([C:10]1[C:11](=[O:35])[N:12]([CH3:34])[C:13]2[C:18]([C:9]=1[NH:8][C:6](=[O:7])[CH2:5][OH:4])=[CH:17][C:16]([C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[C:15]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])[N:14]=2)(=[O:38])[CH3:37]

Participants

6

Reactant 2

HCID 10796Cesium carbonateHCID 113651622-{[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]amino}-2-oxoethyl acetate

Product 1

HCID 11341568N-(3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)-2-hydroxyacetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of EXAMPLE 33 (77 mg) in CH2Cl2 (2 mL) was added Cs2CO3 (43.7 mg) in methanol (1 mL). The reaction stirred at room temperature for 2.5 hours before diluting with EtOAc. The reaction was washed with brine and 10% aqueous NaHSO4 solution. The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-65% EtOAc in hexane affording the title compound. HPLC/MS: 530.1 (M+1), 532.1 (M+3); Rt=3.85 min.

Workup

  1. washThe reaction was washed with brine and 10% aqueous NaHSO4 solution
  2. customThe concentrated residue was purified by flash chromatography on silica gel gradient
  3. washeluted with 0-65% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-74d4c706bcee4ce2953a21464753b898
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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