1,1'-Carbonyldiimidazole → 2-(2-(phenylsulfonyl)ethylthio)-N-(1-(3-(trifluoromethyl)phenyl)ethyl)nicotinamide

HRID 660056ノート

反応式

HRID 660056 の反応式
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]1([S:19]([CH2:22][CH2:23][S:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([OH:29])=O)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:37]=[C:38]([CH:42]([NH2:44])[CH3:43])[CH:39]=[CH:40][CH:41]=1.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[C:13]1([S:19]([CH2:22][CH2:23][S:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([NH:44][CH:42]([C:38]2[CH:39]=[CH:40][CH:41]=[C:36]([C:35]([F:34])([F:45])[F:46])[CH:37]=2)[CH3:43])=[O:29])(=[O:20])=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 2782448(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamineHCID 28213502-[2-(Phenylsulfonyl)ethylthio]nicotinic acidHCID 21226206Ethyl acetate hexane

生成物 1

HCID 252215192-(2-(phenylsulfonyl)ethylthio)-N-(1-(3-(trifluoromethyl)phenyl)ethyl)nicotinamide収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

264 mg (1.62 mmol) of CDI were added to a solution of 500 mg (1.55 mmol) of 2-(2-(phenylsulfonyl)ethylthio)nicotinic acid in DCM (12 ml), and the mixture was stirred for 1 h at RT. A solution of 292 mg (1.55 mmol) of 1-(3-(trifluoromethyl)phenyl)ethylamine in DCM (12 ml) was then added, and stirring was continued for a further 16 h at RT. The reaction solution was then washed in each case three times with sat. aq. ammonium chloride solution and saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC with the residue (ethyl acetate/hexane 1:1) yielded 462 mg (0.93 mmol, 60%) of 2-(2-(phenylsulfonyl)ethylthio)-N-(1-(3-(trifluoromethyl)phenyl)ethyl)nicotinamide. MS: m/z 495.1 [M+H]+.

後処理

  1. stirringstirring
  2. waitwas continued for a further 16 h at RT
  3. washThe reaction solution was then washed in each case three times with sat. aq. ammonium chloride solution and saturated aqueous NaCl solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-90994e99c2244041a6db803193f84607
出典データセット
uspto-grants-2011_12
特許番号
US08084470B2

反応ノート

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