Triethylamine → N-(3-(6-chloro-4-iodopyridin-2-ylamino)cyclohexyl)cyclopropanesulfonamide

HRID 2089055

Reaktionsgleichung

Reaktionsgleichung von HRID 2089055
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH2:15])[CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1.C(N(CC)CC)C.[CH:24]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25]1>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][S:27]([CH:24]3[CH2:26][CH2:25]3)(=[O:29])=[O:28])[CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 86649873N1-(6-chloro-4-iodopyridin-2-yl)cyclohexane-1,3-diamine

Produkt 1

HCID 87191790N-(3-(6-chloro-4-iodopyridin-2-ylamino)cyclohexyl)cyclopropanesulfonamideAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of Example 260a (0.320 g, 0.910 mmol) in DMF (6 mL) were added triethylamine (0.165 mL, 1.183 mmol) and cyclopropanesulfonyl chloride (0.102 mL, 1.001 mmol). The reaction mixture was stirred at room temperature overnight, quenched with brine and NaHCO3 and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with hexane/EtOAc (7:3 to 1:1) to give 0.092 g of the title compound.

Aufarbeitung

  1. customquenched with brine and NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on a 40 g column
  7. washeluting with hexane/EtOAc (7:3 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1812198d119c44dfbd88a853247dc70f
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435980B2

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