2-Methoxyethanol → HCID 178496145, Verbindung

HRID 518689

Reaktionsgleichung

Reaktionsgleichung von HRID 518689
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[CH:14]=[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[C:12]([N+:28]([O-:30])=[O:29])=[CH:11][N:10]=1>C1COCC1>[CH:25]([NH:24][C:22]([C@H:19]1[CH2:20][CH2:21][C@@H:16]([NH:15][C:13]2[C:12]([N+:28]([O-:30])=[O:29])=[CH:11][N:10]=[C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:14]=2)[CH2:17][CH2:18]1)=[O:23])([CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 178457831HCID 178457831, Verbindung

Produkt 1

HCID 178496145HCID 178496145, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice-bath cooled solution of 2-methoxyethanol (0.296 mL, 3.76 mmol) in THF (2.3 mL) was added sodium hydride (150 mg, 3.76 mmol), and the mixture was stirred for 20 minutes. To the mixture was added cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (400 mg, 1.174 mmol), and the flask was removed from the ice bath and the reaction was stirred for 2 hours. The reaction was quenched with water and diluted with DCM, washed with water, saturated aqueous NaHCO3, and the organic layer dried over Na2SO4 and filtered through Celite® brand filter aid. The material was purified via flash chromatography using a linear gradient of 0% to 5% of 1% NH4OH in MeOH in CH2Cl2. The title compound was collected as a yellow solid (273 mg, 61% yield).

Aufarbeitung

  1. customthe flask was removed from the ice bath
  2. stirringthe reaction was stirred for 2 hours
  3. customThe reaction was quenched with water
  4. additiondiluted with DCM
  5. washwashed with water, saturated aqueous NaHCO3
  6. dry with materialthe organic layer dried over Na2SO4
  7. filtrationfiltered through Celite® brand
  8. filtrationfilter aid
  9. customThe material was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bae4857bdfb74c88bd301c7c4c41f6dc
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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