Hydrochloric Acid → 4-Amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 13805Notes

Reaction equation

HRID 13805 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]([CH3:26])[C:13](=[O:27])[C:12](C(O)C)=[C:11]3[NH:31]C(=O)C)=[CH:4][CH:3]=1.O1CCOCC1.Cl>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]([CH3:26])[C:13](=[O:27])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 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 112241864-Amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 3 (21 mg) was combined with 2.8 mL of 1,4-dioxane and 1 mL 1M aqueous HCl. After 15 hours at room temperature the reaction was diluted with EtOAc and washed with water followed by saturated aqueous NaHCO3 solution before drying (Na2SO4). The concentrated residue was purified by preparative TLC (silica gel) eluted with EtOAc affording the title compound. HPLC/MS: 430.0 (M+1), 432.0 (M+3); Rt=3.77 min.

Workup

  1. washwashed with water
  2. dry with materialbefore drying (Na2SO4)
  3. customThe concentrated residue was purified by preparative TLC (silica gel)
  4. washeluted with EtOAc affording the title compound

Sources & evidence

ORD record
ord-2b114d4800d84a4094797752cacaad4b
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

Loading…