Cesium carbonate → HCID 131723668, Verbindung

HRID 31759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31759
CN(C)/[CH:3]=[C:4](\[C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)=O.Cl.[C:22]([NH:25][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[NH:24])[NH2:23].C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[C:32]([O:31][C:29]([NH:28][CH2:27][CH2:26][NH:25][C:22]1[N:23]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=2)[C:4]([C:15]2[NH:19][CH:18]=[CH:17][N:16]=2)=[CH:3][N:24]=1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 693105754-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrileHCID 178453692HCID 178453692, Verbindung

Produkt 1

HCID 131723668HCID 131723668, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile (8.0 g, 30.0 mmol) in NMP (5 ml) was added to a stirred mixture of N-[2-(amidinoamino)ethyl](tert-butoxy)carboxamide, hydrochloride (13.8 g, 45 mmol)) and Cs2CO3 (11.72, 36.0 mmol) in NMP (15 ml). The reaction was heated to 100° C. for 48 hours. The reaction was followed by HPLC. Upon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml). The organic layer was separated and washed with water (2×50 ml), brine (50 ml), dried Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography eluting with 10% methanol in dichloromethane. After stripping off the solvents and drying in vacuo, 10.08 g of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide was obtained as a dark red glass in 83% yield.

Aufarbeitung

  1. customUpon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml)
  2. customThe organic layer was separated
  3. washwashed with water (2×50 ml), brine (50 ml), dried Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by flash chromatography
  7. washeluting with 10% methanol in dichloromethane
  8. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-658e4343c5a540c6ad60ea0d34b51c8b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425557B2

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