Dimethylformamide → N-Cyclopropyl-N-[1-(2-nitro-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 1428960

反応式

HRID 1428960 の反応式
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH:24]1[CH:25]=[CH:26][C:27]2[N:32]([OH:33])N=N[C:28]=2[CH:29]=1.CCN=C=NCCCN(C)C.[N+]([O:48][C:49](=O)C1C=CC=CC=1)([O-])=O.CN(C=[O:61])C>>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:49](=[O:48])[C:28]3[CH:29]=[CH:24][CH:25]=[CH:26][C:27]=3[N+:32]([O-:33])=[O:61])[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 12282512Nitro benzoate

生成物 1

HCID 24860818N-Cyclopropyl-N-[1-(2-nitro-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide収率 93%

実験手順

N-Cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (0.348 g, 1.0 mmol), HOBt (0.135 g, 1.0 mmol), EDCI (0.230 g, 1.2 mmol) and O-nitrobenzoic acid (0.184 g, 1.1 mmol) were dissolved in 10 ml of dry DMF. The mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was concentrated and dryness under reduced pressure. Then the residue was dissolved in EtOAc (50 ml) and the mixture was washed with saturated NaHCO3 (30 ml) and brine (30 ml). The organic layer was dried over MgSO4 and concentrated to dryness. The crude product was purified through a column of silica gel with a gradient of 65% to 80% EtOAc in hexane to afford the title compound 10 (pale yellow solid, 462 mg, 93%). LC: 97%. MS: m/z=497.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThen the residue was dissolved in EtOAc (50 ml)
  3. washthe mixture was washed with saturated NaHCO3 (30 ml) and brine (30 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified through a column of silica gel with a gradient of 65% to 80% EtOAc in hexane

出典と根拠

ORDレコード
ord-c189aa789d4b4f5a9fdc59bc8325994a
出典データセット
uspto-grants-2015_01
特許番号
US08937181B2

関連ノート

読み込み中…