3,3,3-Trifluoropropane-1-sulfonyl chloride → N-((1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)-3, 3, 3-trifluoropropane-1-sulfonamide

HRID 1969600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969600
[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[CH:11]1[C:19]2[N:18]3[C:20]([CH:23]4[CH:27]([CH3:28])[CH2:26][CH:25]([NH2:29])[CH2:24]4)=[CH:21][N:22]=[C:17]3[CH:16]=[N:15][C:14]=2[NH:13][CH:12]=1>CN(C=O)C>[CH:11]1[C:19]2[N:18]3[C:20]([C@@H:23]4[C@H:27]([CH3:28])[CH2:26][C@H:25]([NH:29][S:5]([CH2:4][CH2:3][C:2]([F:10])([F:9])[F:1])(=[O:7])=[O:6])[CH2:24]4)=[CH:21][N:22]=[C:17]3[CH:16]=[N:15][C:14]=2[NH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 27611773,3,3-Trifluoropropane-1-sulfonyl chlorideHCID 585571313-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine

Produkt 1

HCID 67999398N-((1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)-3, 3, 3-trifluoropropane-1-sulfonamideAusbeute 5,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3,3,3-Trifluoropropane-1-sulfonyl chloride (0.194 g, 0.987 mmol, Matrix) was added dropwise to a solution of TEA (0.31 mL, 2.2 mmol) and 3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine (0.28 g, 1.1 mmol, Preparation #53) in DMF (10 mL). The resulting mixture was stirred at ambient temperature for about 144 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water (20 mL each). The layers are separated and the organic layer was washed with brine (30 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The residue was purified by using General Procedure AA (Table 2, Method 9, Rt=17.7 min, or =negative) to give N-((1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)-3,3,3-trifluoropropane-1-sulfonamide (0.021 g, 4.6%) as a white solid: LC/MS (Table 1, Method a) Rt=1.79 min; MS m/z 416 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and water (20 mL each)
  3. customThe layers are separated
  4. washthe organic layer was washed with brine (30 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-b4bdbc623644483dbe1fac7da067fe59
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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