Cyclopentanone → HCID 66743184、化合物

HRID 2364040ノート

反応式

HRID 2364040 の反応式
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=[O:8])=[C:4]([NH:10][CH2:11][CH3:12])[CH:3]=1.[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:8])[NH:9][C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[N:10]([CH2:11][CH3:12])[C:4]=2[CH:3]=1

参加物

7

反応物 5

HCID 8452CyclopentanoneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 66743701HCID 66743701、化合物

生成物 1

HCID 66743184HCID 66743184、化合物収率 56%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 5-bromo-3-(ethylamino)thiophene-2-carboxamide (500 mg, 2.0 mmol), cyclopentanone (0.53 mL, 6.0 mmol), CSA (46 mg, 0.20 mmol), MgSO4 (384 mg, 4.0 mmol) and DMA (1.5 mL) was stirred at 90° C. for 1 day. The mixture was poured into saturated aqueous NaHCO3. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 50:50 hexane/EtOAc) to give a brown solid. The solid was washed with EtOAc to give the title compound (352 mg, 56%) as a pale brown solid:

後処理

  1. extractionThe organic materials were extracted with EtOAc
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customAfter removal of the solvent at reduced pressure
  6. customthe residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 50:50 hexane/EtOAc)
  7. customto give a brown solid
  8. washThe solid was washed with EtOAc

出典と根拠

ORDレコード
ord-c5a90e1123274a33af7521819fb29104
出典データセット
uspto-grants-2014_04
特許番号
US08691828B2

反応ノート

読み込み中…