Hydrochloric Acid → 3-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 13803

反応式

HRID 13803 の反応式
[C:1]([C:4]1[C:5](=[O:34])[N:6]([CH3:33])[C:7]2[C:12]([C:13]=1[NH:14]C(=O)C)=[CH:11][C:10]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[C:9]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])[N:8]=2)(=[O:3])[CH3:2].Cl>O1CCOCC1.CCOC(C)=O>[C:1]([C:4]1[C:5](=[O:34])[N:6]([CH3:33])[C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][C:10]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[C:9]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])[N:8]=2)(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 313Hydrochloric Acid2 回HCID 11386747Naphthyridinone

生成物 1

HCID 112600073-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

To 16 mg of the product of Example 1 in 1,4-dioxane (1 mL) was added 0.5 mL of 1 M aqueous HCl solution. The reaction stirred at 50° C. for 5 hours. LC/MS indicated little product forming and an additional 0.2 mL of concentrated HCl solution was added. The temperature was increased to 90° C. for 4.5 hours at which point the reaction was cooled to room temperature and diluted with EtOAc. The solution was washed with saturated aqueous NaHCO3 solution before drying with Na2SO4 and concentrating. The residue was purified by preparative TLC (silica gel) eluted with 20% EtOAc in CH2Cl2 affording the title compound. HPLC/MS: 471.9 (M+1), 473.9 (M+3); Rt=4.32 min.

後処理

  1. customforming
  2. temperatureThe temperature was increased to 90° C. for 4.5 hours at which
  3. temperaturewas cooled to room temperature
  4. washThe solution was washed with saturated aqueous NaHCO3 solution
  5. dry with materialbefore drying with Na2SO4
  6. concentrationconcentrating
  7. customThe residue was purified by preparative TLC (silica gel)
  8. washeluted with 20% EtOAc in CH2Cl2 affording the title compound

出典と根拠

ORDレコード
ord-c547244f2ee541b2b0328425718be039
出典データセット
uspto-grants-2010_06
特許番号
US07728141B2

関連ノート

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