Potassium Carbonate → N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-(2-hydroxyethoxy)ethoxy)-5-methylbenzamide

HRID 1890137

反応式

HRID 1890137 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[OH:28])[CH2:7][CH2:6]2.Cl[CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36])[CH2:7][CH2:6]2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 16738306N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-hydroxy-5-methylbenzamide

生成物 1

HCID 68008900N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-(2-hydroxyethoxy)ethoxy)-5-methylbenzamide収率 52.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The mixture of 4a (0.65 g, 1.6 mmol), 2-(2-chloroethoxy)ethanol (0.64 g, 5.1 mmol), potassium carbonate (0.71 g, 5.1 mmol) in of N,N-Dimethylformamide (DMF) (25 mL) was refluxed over night under an atmosphere of nitrogrn. The reaction mixture was cooled to room temperature and quenched with 100 mL water. The aqueous solution was extracted with ethyl acetate (3 X2 50 mL). The combined organic layer was washed with brine (3×30 mL) and dried over Na2SO4. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography with methanol/dichloromethane (10/90, v/v) as the mobile phase to afford compound 5a (0.41 g; 51% yield) as a viscous yellow oil. 1H NMR (300 MHz, CDCl3): 1.68-1.79 (m, 4H), 2.31 (s, 3H), 2.50-2.60 (m, 2H), 2.72-2.76 (m, 2H), 2.82-2.85 (m, 2H), 3.46-3.60 (m, 8H), 3.80-3.90 (m, 8H), 4.18-4.24 (m, 2H), 6.49 (s, 1H), 6.58 (s, 1H), 6.79-6.83 (d, 1H), 7.16-7.24 (m, 1H), 7.98-7.80 (m, 1H), 8.18-8.26 (s, 1H).

後処理

  1. temperaturewas refluxed over night under an atmosphere of nitrogrn
  2. customquenched with 100 mL water
  3. extractionThe aqueous solution was extracted with ethyl acetate (3 X2 50 mL)
  4. washThe combined organic layer was washed with brine (3×30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrating under reduced pressure
  7. customthe residue was purified by silica gel column chromatography with methanol/dichloromethane (10/90

出典と根拠

ORDレコード
ord-15c68c1c5c5e4195b30dcf7e0b2b75d2
出典データセット
uspto-grants-2013_08
特許番号
US08506927B2

関連ノート

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