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Cesium carbonate → (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyridin-2-ylamino)butanamide

HRID 84868
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 84868
[NH2:1][C:2](=[O:27])[C@H:3]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=O)=[C:9](NC2C=NC3C(C=2)=CC=CC=3)[N:8]=1)[CH2:4][CH3:5].[NH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]([C:10]1[CH:14]=[CH:15][C:7]([NH:6][C@H:3]([CH2:4][CH3:5])[C:2]([NH2:1])=[O:27])=[N:8][C:9]=1[NH:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2)#[N:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 113736-AminoquinolineHCID 634876Binap, (A+-)-HCID 67516146(R)-6-(1-amino-1-oxobutan-2-ylamino)-2-(quinolin-3-ylamino)nicotinamide

Produkt 1

HCID 67775481(R)-2-(5-cyano-6-(quinolin-6-ylamino)pyridin-2-ylamino)butanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

The mixture of (R)-2-(6-chloro-5-cyanopyridin-2-ylamino)butanamide (compound J52 in Example 203) (140 mg, 0.59 mmol), 6-aminoquinoline (260 mg, 1.8 mmol), cesium carbonate (980 mg, 3.0 mmol), BINAP (75 mg, 0.12 mmol) and Pd(OAc)2 (27 mg, 0.12 mmol) in 20 mL dioxane was degassed with Ar. The mixture was stirred under Ar at 105° C. for overnight. It was concentrated in vacuo, taken into EtOAc, washed with brine, dried, concentrated in vacuo and subjected to flash column (0 to 8% MeOH in DCM) to isolate (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyridin-2-ylamino)butanamide. It was then dissolved in 4 mL DMSO. To it were added 100 mg powder K2CO3 and 2 mL 50% H2O2 in water. The mixture was stirred at RT for 1 h. To it was added 4 mL water, the mixture was vigorously stirred and subjected to reverse phase preparative HPLC to isolate the title compound (65 mg). UV: 267, 299, 330 nm. M+H found for C19H20N6O2: 365.2. NMR (CD3OD): 9.25 (1H, d, J=8.8 Hz), 9.04 (1H, d, J=2.0 Hz), 8.85 (1H, dd, J=6.4; 2.4Hz), 8.06 (1H, d, J=9.6 Hz), 7.99 (1H, dd, J=9.2; 2.41 Hz), 7.92 (1H, m), 7.88 (1H, d, J=8.8 Hz), 6.28 (1H, d, J=9.2 Hz), 4.31 (1H, m), 2.00 (2H, m), 1.14 (3H, t, J=7.6 Hz) ppm.

Aufarbeitung

  1. customwas degassed with Ar
  2. concentrationIt was concentrated in vacuo
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-371a40ab37c14a8ba06d21bc29e439fc
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846928B2

Notizen zur Reaktion

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