Methanol → N-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1,3-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]propanamide

HRID 13821Notes

Reaction equation

HRID 13821 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:18]=[C:17]2[C:12]([C:13]([N:22](C(=O)CC)[C:23](=[O:26])[CH2:24][CH3:25])=[C:14]([CH3:21])[C:15](=[O:20])[N:16]2[CH3:19])=[CH:11][C:10]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1.CO.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CCOC(C)=O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:10]2[CH:11]=[C:12]3[C:17](=[N:18][C:9]=2[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:16]([CH3:19])[C:15](=[O:20])[C:14]([CH3:21])=[C:13]3[NH:22][C:23](=[O:26])[CH2:24][CH3:25])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10796Cesium carbonateHCID 68717076N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1,3-dimethyl-2-oxo-1,8-naphthyridin-4-yl)-N-propionylpropionamide

Product 1

HCID 11249076N-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1,3-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]propanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of step A (1.56 g) in THF (12 mL) was added methanol (3 mL) and Cs2CO3. The reaction stirred overnight at room temperature before it was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution. The concentrated residue was purified by flash chromatography on silica gel with an EtOAc/hexane gradient elution affording the title compound. HPLC/MS: 499.8 (M+1), 501.8 (M+3); Rt=3.95 min.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution
  2. customThe concentrated residue was purified by flash chromatography on silica gel with an EtOAc/hexane gradient elution

Sources & evidence

ORD record
ord-79414734ff2b4854aa0fab7efffa5578
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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