Potassium Carbonate → (R)-2-(4-cyano-3-(5-methylisoxazol-3-ylamino)phenylamino)-4-methylpentanamide

HRID 84810

Reaktionsgleichung

Reaktionsgleichung von HRID 84810
Br[C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([NH2:14])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[NH2:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1.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.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([NH:10][C@H:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([NH2:14])=[O:13])=[CH:3][C:2]=1[NH:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1)#[N:9]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 661723-Amino-5-methylisoxazoleHCID 634876Binap, (A+-)-HCID 67509372(R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide

Produkt 1

HCID 67510964(R)-2-(4-cyano-3-(5-methylisoxazol-3-ylamino)phenylamino)-4-methylpentanamideAusbeute 19,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A mixture of (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide (120 mg, 0.387 mmol), 3-amino-5-methylisoxazole (60 mg, 0.612 mmol), BINAP (40 mg, 0.064 mmol), Pd(OAc)2 (30 mg, 0.13 mmol) and K2CO3 (150 mg, 1.08 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 120 C for 18 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(4-cyano-3-(5-methylisoxazol-3-ylamino)phenylamino)-4-methylpentanamide (25 mg).

Aufarbeitung

  1. customwas degassed with Ar
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-564a0593e8774134aa927e1dae04c80e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846928B2

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