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

HRID 13833
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HRID 13833 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4e17fddd3367487296d105c888614ea4
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728141B2

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