Dimethylformamide → Methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate

HRID 926049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926049
[CH3:1][Si:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([S:14]([NH:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=2)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1)=[O:7].CN(C=O)C.I[CH2:36][CH2:37][CH3:38].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:36]([N:17]([S:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:6]([O:5][CH2:4][CH2:3][Si:2]([CH3:28])([CH3:1])[CH3:29])=[O:7])[CH:9]=1)(=[O:15])=[O:16])[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=1)[CH2:37][CH3:38]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 71238735Methyl 6-{[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate

Produkt 1

HCID 71238187Methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 500 mg of methyl 6-{[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate and 10 mL of DMF were added 0.300 mL of 1-iodopropane and 400 mg of potassium carbonate, followed by stirring at 80° C. for 5 hours. The reaction mixture was left to stand to cool and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (chloroform-ethyl acetate) to obtain 200 mg of a methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate as a colorless oily substance. ESI+: 479

Aufarbeitung

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9aae2aa85cc241c5a3ebe874f2942656
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284295B2

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