1-Bromo-2-Chloroethane → 3-[7-(2-Chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide

HRID 507013ノート

反応式

HRID 507013 の反応式
[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].Br[CH2:26][CH2:27][Cl:28].[C:29](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:28][CH2:27][CH2:26][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][CH:1]3[CH2:29][CH2:2]3)=[O:24])[C:13]2=[O:23])=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 11674186N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

生成物 1

HCID 670185703-[7-(2-Chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (0.65 g), 1-bromo-2-chloroethane (0.8 ml) and potassium carbonate (2.6 g) were stirred in DMF (26 ml) at 50° C. for 23 hours. The reaction mixture was diluted with ethyl acetate and washed with water (×5), brine (×2), dried (magnesium sulfate) and concentrated to give 3-[7-(2-chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide as a foam (577 mg); NMR Spectrum: (DMSO d6) 1.17 (t, 3H), 2.16 (s, 3H), 3.34 (m, 2H), 4.05 (t, 2H), 4.45 (m, 2H), 6.80 (d, 1H), 7.30 (d, 1H), 7.53 (m, 2H), 7.74 (d, 1H), 7.82 (m, 2H), 7.94 (d, 1H), 8.51 (t, 1H); Mass Spectrum: M+H+ 385.

後処理

  1. washwashed with water (×5), brine (×2)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-d52b6c39bb3c47cea5d16ec064d102a9
出典データセット
uspto-grants-2010_08
特許番号
US07786115B2

反応ノート

読み込み中…