Potassium Carbonate → 2-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide

HRID 660058

반응식

HRID 660058 반응식
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:22]=[CH:21][CH:20]=[CH:19][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[O:11].Br[CH2:24][CH2:25][S:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(OCC)(=O)C.CCCCCC>CN(C=O)C.C(OCC)(=O)C.O>[CH:27]1([S:26][CH2:25][CH2:24][S:7][C:8]2[N:22]=[CH:21][CH:20]=[CH:19][C:9]=2[C:10]([NH:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 22455667((2-Bromoethyl)thio)cyclohexaneHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

생성물 1

HCID 252216282-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide수율 34%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

607 mg (4.4 mmol) of K2CO3 were added to a solution of 500 mg (2.0 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide (V1) in DMF (5 ml), and the mixture was stirred for 1 h at RT. 446 mg of (2-bromoethyl)-(cyclohexyl)sulfane (crude product V2) were then added, and stirring was continued for a further 18 h at RT. The mixture was then diluted with ethyl acetate, and water was added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. CC (ethyl acetate/n-hexane 1:1) with the residue yielded 268 mg (0.68 mmol, 34%) of 2-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide. MS: m/z 393.1 [M+H]+.

후처리

  1. stirringstirring
  2. waitwas continued for a further 18 h at RT
  3. additionwas added
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-94ddc86d71c64fd888d40ac1c2768cdd
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084470B2

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