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Sodium Iodide → 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide

HRID 506973
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HRID 506973 반응식
[CH2:1]([NH:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=3)[C:13]2=[O:23])[CH:6]=1)[CH3:2].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[CH:21][N:12]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=3[CH3:11])[C:4]([NH:3][CH2:1][CH3:2])=[O:24])[C:13]2=[O:23])=[CH:18][CH:17]=1
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참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 11674186N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

생성물 1

HCID 116325883-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (88 mg), 2-dimethylaminoethyl chloride hydrochloride (51 mg), potassium carbonate (0.38 g), and sodium iodide (3 mg) were stirred in acetone (4 ml) at 60° C. for 17 hours. The reaction mixture was filtered, the solids washed with acetone, and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 2N NaOH solution, brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica-column eluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution gave 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide as a white solid; NMR Spectrum: (DMSOd6) 1.11 (t, 3H), 2.10 (s, 3H), 2.24 (s, 6H), 2.68 (t, 2H), 3.28 (m, 2H), 4.18 (m, 2H), 6.72 (d, 1H), 7.21 (d, 1H), 7.41 (d, 1H), 7.50 (d, 1H), 7.69 (s, 1H), 7.71 (d, 1H), 7.78 (s, 1H), 7.89 (d, 1H), 8.48 (s, 1H); Mass Spectrum: M+H+ 394.

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed with acetone
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 2N NaOH solution, brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customPurification by column chromatography on a silica-column
  9. washeluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution

출처 및 근거

ORD 기록
ord-714e12ab53134fe0bbe96d938569dd17
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786115B2

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