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Triethylamine → HCID 58970687, Verbindung

HRID 598043
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598043
C(N(CC)CC)C.Cl.Cl.[NH2:10][C:11]([CH3:33])([CH3:32])[CH2:12][N:13]1[C:25]2[C:24]3[N:23]=[CH:22][C:21]([Br:26])=[CH:20][C:19]=3[N:18]=[C:17]([NH2:27])[C:16]=2[N:15]=[C:14]1[CH2:28][O:29][CH2:30][CH3:31].[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[NH2:27][C:17]1[C:16]2[N:15]=[C:14]([CH2:28][O:29][CH2:30][CH3:31])[N:13]([CH2:12][C:11]([NH:10][S:35]([CH3:34])(=[O:37])=[O:36])([CH3:32])[CH3:33])[C:25]=2[C:24]2[N:23]=[CH:22][C:21]([Br:26])=[CH:20][C:19]=2[N:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 670524671-(2-amino-2-methylpropyl)-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine dihydrochloride

Produkt 1

HCID 58970687HCID 58970687, VerbindungAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
3×

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

Triethylamine (13.02 g, 128.7 mmol) was added to a suspension of 1-(2-amino-2-methylpropyl)-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine dihydrochloride (6.00 g, 12.9 mmol) in dichloromethane (500 mL), and the reaction was cooled to 4° C. A solution of methanesulfonyl chloride (1.62 g, 14.2 mmol) in dichloromethane (10 mL) was then added dropwise. The reaction mixture was allowed to warm to room temperature, stirred for 24 hours, diluted with dichloromethane (200 mL), washed sequentially with water (200 mL), 4% aqueous sodium carbonate (2×200 mL), water (200 mL), and brine (200 mL), and concentrated under reduced pressure. The crude product was purified by automated flash chromatography (FLASH 40+M silica cartridge, eluting with 0 to 25% CMA in chloroform) followed by recrystallization from acetonitrile to provide 5.21 g of N-{2-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-1,1-dimethylethyl}methanesulfonamide as a white solid, 211-212° C.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. washwashed sequentially with water (200 mL), 4% aqueous sodium carbonate (2×200 mL), water (200 mL), and brine (200 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by automated flash chromatography (FLASH 40+M silica cartridge, eluting with 0 to 25% CMA in chloroform)
  5. customfollowed by recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-d640c6207a2e40ac80b55b81bc506394
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897609B2

Notizen zur Reaktion

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