Sodium Iodide → n-Cyclohexyl-2-(6-methyl-6-{3-[(methylsufonyl)amino]phenyl}-3-azabicyclo[3.1.0]hex-3-yl)acetamide

HRID 428869ノート

反応式

HRID 428869 の反応式
[CH3:1][C:2]1([C:8]2[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:7]2[CH:3]1[CH2:4][NH:5][CH2:6]2.C(=O)([O-])O.[Na+].Cl[CH2:25][C:26]([NH:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:27].[I-].[Na+]>CN(C)C=O.O.C(OCC)C>[NH3:5].[CH:29]1([NH:28][C:26](=[O:27])[CH2:25][N:5]2[CH2:6][CH:7]3[CH:3]([C:2]3([CH3:1])[C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=3)[CH2:4]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

参加物

9

反応物 4

HCID 5238Sodium IodideHCID 2223652-Chloro-N-cyclohexylacetamideHCID 516892Sodium BicarbonateHCID 22141143N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamide

生成物 2

HCID 222AmmoniaHCID 22141352n-Cyclohexyl-2-(6-methyl-6-{3-[(methylsufonyl)amino]phenyl}-3-azabicyclo[3.1.0]hex-3-yl)acetamide収率 57.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 57 mg, 0.19 mmol) in N,N-dimethylformamide (2 ml) was added sodium hydrogen carbonate (630 mg, 7.52 mmol), 2-chloro-N-cyclohexylacetamide (36 mg, 0.2 mmol) and sodium iodide (catalytic) and the reaction was heated at 50° C. for 20 h. After cooling diethyl ether (5 ml) and water (7 ml) were added and the reaction mixture was stirred vigorously for 5 min. The phases were separated and the aqueous layer was further extracted with diethyl ether (2×5 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residual oil was purified by flash column chromatography using a Sep-Pak™ cartridge packed with silica gel (5 g) eluting with dichloromethane:ethanol:0.88 ammonia solution (200:8:1) to afford the title compound as an oil (22 mg, 28%).

後処理

  1. additionwere added
  2. customThe phases were separated
  3. extractionthe aqueous layer was further extracted with diethyl ether (2×5 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was purified by flash column chromatography
  8. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-a6d729ad0be44e8b813b00505099e9be
出典データセット
uspto-grants-2001_11
特許番号
US06313312B1

反応ノート

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