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Dimethylamine → 3-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide

HRID 2267510
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2267510
Cl[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5].[CH3:31][NH:32][CH3:33].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[CH3:31][N:32]([CH3:33])[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 590033063-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Produkt 1

HCID 114962033-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamideAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide (26 mg, 0.063 mmol) in CH3CN (5 mL), dimethylamine (0.16 mL, 0.315 mmol), K2CO3 (35 mg, 0.252 mmol) and NaI (cat. 0.5 mg) were added. The reaction mixture was stirred at 80° C. for 16 hours. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA) to give title compound (14 mg, 48%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-75ff698322674d04811461320869195c
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07858796B2

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