Potassium Carbonate → HCID 67509932, Verbindung

HRID 2201130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201130
Br[C:2]1[C:3]([C:27]#[N:28])=[CH:4][C:5]([F:26])=[C:6]([NH:8][C@H:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[C:10]([NH2:12])=[O:11])[CH:7]=1.Cl.[NH2:30][C:31]1[S:35][N:34]=[C:33]([CH3:36])[CH:32]=1.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.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:27]([C:3]1[C:2]([NH:30][C:31]2[S:35][N:34]=[C:33]([CH3:36])[CH:32]=2)=[CH:7][C:6]([NH:8][C@H:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[C:10]([NH2:12])=[O:11])=[C:5]([F:26])[CH:4]=1)#[N:28]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 67508174(R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-(4-(pyridin-4-yl)phenyl)propanamide

Produkt 1

HCID 67509932HCID 67509932, VerbindungAusbeute 18,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-(4-(pyridin-4-yl)phenyl)propanamide (62 mg, 0.14 mmol), 5-amino-3-methylisothiazole hydrochloride (35 mg, 0.23 mmol), K2CO3 (65 mg, 0.47 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) and water (0.1 mL) was degassed with argon, then was stirred at 120 C for 18 h. The mixture was purified by HPLC to give (R)-2-(4-cyano-2-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)-3-(4-(pyridin-4-yl)phenyl)propanamide (12 mg).

Aufarbeitung

  1. customwas degassed with argon
  2. customThe mixture was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1e42bc91fdf84759be319ac0435a1f9d
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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