6-Aminoquinoline → (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-2-phenylacetamide

HRID 2200477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200477
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=1[C:19]#[N:20].[NH2:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[CH:25]2.C([O-])([O-])=O.[K+].[K+].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:19]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@H:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([NH2:12])=[O:11])=[N:7][C:2]=1[NH:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[CH:25]2)#[N:20]

Komponenten

7

Edukt 4

HCID 113736-AminoquinolineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 86685593(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-2-phenylacetamide

Produkt 1

HCID 86685594(R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-2-phenylacetamideAusbeute 13,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-2-phenylacetamide (81 mg, 0.281 mmol), 6-aminoquinoline (60 mg, 0.416 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-2-phenylacetamide (15 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-620f386a94c048bf8c6f740370bf5a40
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359308B2

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