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

HRID 13803

반응식

HRID 13803 반응식
[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]

참가 물질

5

반응물 2

HCID 313Hydrochloric Acid2회HCID 11386747Naphthyridinone

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c547244f2ee541b2b0328425718be039
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728141B2

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