Methanol → 4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-3-(1-methoxyethyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 13833Notes

Reaction equation

HRID 13833 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[N:14](C)[C:13](=O)[C:12]([CH:28]([OH:30])[CH3:29])=[C:11]3[NH:31]C(=O)C)=[CH:4][CH:3]=1.[CH3:35]S(Cl)(=O)=O.C(N(CC)CC)C.[CH3:47][OH:48]>C1COCC1.CCOC(C)=O>[NH2:31][C:11]1[C:10]2[C:15](=[N:16][C:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH:9]=2)[N:14]([CH3:13])[C:47](=[O:48])[C:12]=1[CH:28]([O:30][CH3:35])[CH3:29]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11283741N-[6-(4-Chlorophenyl)-7-(2,4-dichlorophenyl)-3-(1-hydroxyethyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

Product 1

HCID 112026224-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-3-(1-methoxyethyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 3 (50 mg) in THF (1 mL) was combined with methansulfonyl chloride (15 μL) and triethylamine (27 μL) at 0° C. The reaction stirred 15 minutes at which point methanol (2 mL) was added. The reaction stirred 4.5 hours before it was diluted with EtOAc and washed with water. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluted with 0-20% EtOAc in hexane afforded the title compound. HPLC/MS: 488.0 (M+1), 490.0 (M+3); Rt=4.45 min.

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica
  7. washeluted with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-4e17fddd3367487296d105c888614ea4
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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