Triethylamine → 2-[2-(3-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamide

HRID 660060

Reaktionsgleichung

Reaktionsgleichung von HRID 660060
[F:1][C:2]1[CH:3]=[C:4]([S:8]([CH2:11][CH2:12]O)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.CS(Cl)(=O)=O.C([O-])([O-])=O.[K+].[K+].[SH:32][C:33]1[N:47]=[CH:46][CH:45]=[CH:44][C:34]=1[C:35]([NH:37][CH2:38][C:39]1[S:40][CH:41]=[CH:42][CH:43]=1)=[O:36]>C(Cl)Cl.CN(C=O)C.CC(=O)OCC.C(Cl)Cl.CC(=O)OCC>[F:1][C:2]1[CH:3]=[C:4]([S:8]([CH2:11][CH2:12][S:32][C:33]2[N:47]=[CH:46][CH:45]=[CH:44][C:34]=2[C:35]([NH:37][CH2:38][C:39]2[S:40][CH:41]=[CH:42][CH:43]=2)=[O:36])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

10

Edukt 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 27591433-FluorophenylsulfonylethanolHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

Produkt 1

HCID 687272312-[2-(3-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

A solution of 408 mg (2.0 mmol) of 2-(3-fluorophenylsulfonyl)ethanol in DCM (5 ml) was cooled to 0° C.; 304 μl (2.2 mmol) of NEt3 and 154 μl (2.0 mmol) of methanesulfonic acid chloride were added thereto, and stirring was carried out for 16 hours at RT. In another vessel, 275 mg (2.0 mmol) of K2CO3 were added to a solution of 500 mg (2.0 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide in DMF (6 ml), and stirring was carried out for 30 min at RT. The DCM reaction solution was added to this solution, and stirring was continued for 72 hours at RT. The mixture was then diluted with EA and washed with 1 N aqueous NaHCO3 solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC (DCM/EA 4:1) of the residue yielded 194 mg (0.44 mmol, 22%) of 2-[2-(3-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamide. MS: m/z 437.0 [M+H]+

Aufarbeitung

  1. stirringstirring
  2. waitwas carried out for 30 min at RT
  3. additionwas added to this solution
  4. stirringstirring
  5. waitwas continued for 72 hours at RT
  6. washwashed with 1 N aqueous NaHCO3 solution
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ffb0c654c7f44716a0a34aa0f4cb972c
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084470B2

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