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

HRID 660056노트

반응식

HRID 660056 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-90994e99c2244041a6db803193f84607
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084470B2

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