Pyridine → HCID 89876288, Verbindung

HRID 594128

Reaktionsgleichung

Reaktionsgleichung von HRID 594128
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])=[N:6][C:7]=1[CH3:8].N1C=CC=CC=1.[CH3:21][C:22]1[C:26]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=2)=[C:25]([CH3:39])[O:24][N:23]=1>ClCCl>[CH3:21][C:22]1[C:26]([CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([S:35]([NH:1][C:2]3[C:7]([CH3:8])=[N:6][C:5]([N:9]4[CH2:13][CH2:12][O:11][C:10]4=[O:14])=[CH:4][CH:3]=3)(=[O:37])=[O:36])=[CH:33][CH:34]=2)=[C:25]([CH3:39])[O:24][N:23]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 898760323-(5-Amino-6-methyl-2-pyridinyl)-1,3-oxazolidin-2-one

Produkt 1

HCID 89876288HCID 89876288, VerbindungAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 3-(5-amino-6-methyl-2-pyridinyl)-1,3-oxazolidin-2-one (80 mg, 0.414 mmol) in dichloromethane (3 mL) and pyridine (0.033 mL, 0.414 mmol) was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (125 mg, 0.414 mmol). The reaction vessel was sealed and heated at 65° C. for 6 hours. The reaction mixture was then allowed to cool and separated between dichloromethane (40 mL) and saturated sodium bicarbonate solution (30 mL). The organic phase was separated using a hydrophobic frit and evaporated in vacuo. The crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title compound (137 mg) as a colourless glassy solid. LCMS (2 min, formic) Rt 0.92 min, m/z (ES+) 459 (M+H).

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperatureto cool
  3. customseparated between dichloromethane (40 mL) and saturated sodium bicarbonate solution (30 mL)
  4. customThe organic phase was separated
  5. customevaporated in vacuo
  6. customThe crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient)
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6df9302049dd4f26b955ab67804c55e5
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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