Water → N-((1S,3R,4S)-3-ethyl-4-(2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h][1,6]naphthyridin-1-yl)cyclopentyl)cyclopropane-sulfonamide

HRID 1969877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969877
[CH2:1]([C@H:3]1[C@@H:7]([N:8]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]4[N:20](S(C5C=CC(C)=CC=5)(=O)=O)[CH:19]=[CH:18][C:16]4=3)[CH2:11][CH2:10][CH2:9]2)[CH2:6][C@@H:5]([NH:31][S:32]([CH:35]2[CH2:37][CH2:36]2)(=[O:34])=[O:33])[CH2:4]1)[CH3:2].[OH-].[Na+].O.CCOC(C)=O>O1CCOCC1>[CH2:1]([C@H:3]1[C@@H:7]([N:8]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]4[NH:20][CH:19]=[CH:18][C:16]4=3)[CH2:11][CH2:10][CH2:9]2)[CH2:6][C@@H:5]([NH:31][S:32]([CH:35]2[CH2:36][CH2:37]2)(=[O:34])=[O:33])[CH2:4]1)[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 58557285N-((1S,3R,4S)-3-ethyl-4-(7-tosyl-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h][1,6]naphthyridin-1-yl)cyclopentyl)cyclopropanesulfonamide

Produkt 1

HCID 53257644N-((1S,3R,4S)-3-ethyl-4-(2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h][1,6]naphthyridin-1-yl)cyclopentyl)cyclopropane-sulfonamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N-((1S,3R,4S)-3-ethyl-4-(7-tosyl-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h][1,6]naphthyridin-1-yl)cyclopentyl)cyclopropanesulfonamide (0.041 g, 0.076 mmol) in 1,4-dioxane was added aqueous NaOH (5 N, 0.106 mL, 0.529 mmol). The reaction was heated to about 80° C. for about 16 h. The reaction mixture was cooled to ambient temperature and water (5 mL) and EtOAc (10 mL) were added. The layers were separated and the aqueous phase was extracted with EtOAc (2×10 mL). The combined organics were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to give N-((1S,3R,4S)-3-ethyl-4-(2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h][1,6]naphthyridin-1-yl)cyclopentyl)cyclopropane-sulfonamide (0.02 g, 72%) as a white solid: LC/MS (Table 1, Method a) Rt=1.48 min; MS m/z: 389 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×10 mL)
  4. dry with materialThe combined organics were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of 0-10% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-c4e641120a354a6c9c1db0ef9b850acb
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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