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

HRID 507013노트

반응식

HRID 507013 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].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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d52b6c39bb3c47cea5d16ec064d102a9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786115B2

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