Cesium carbonate → 4-(1-Phenylcyclopropylamino)-6-(4-(4-propionylpiperazin-1-yl)phenylamino)nicotinamide

HRID 513273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513273
Cl[C:2]1[CH:10]=[C:9]([NH:11][C:12]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13]2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([C:34](=[O:37])[CH2:35][CH3:36])[CH2:30][CH2:29]2)=[CH:24][CH:23]=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.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:15]1([C:12]2([NH:11][C:9]3[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=[C:2]([NH:21][C:22]4[CH:23]=[CH:24][C:25]([N:28]5[CH2:29][CH2:30][N:31]([C:34](=[O:37])[CH2:35][CH3:36])[CH2:32][CH2:33]5)=[CH:26][CH:27]=4)[CH:10]=3)[CH2:14][CH2:13]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 9347841-(4-(4-Aminophenyl)piperazin-1-yl)propan-1-oneHCID 866645416-Chloro-4-(1-phenylcyclopropylamino)nicotinamide

Produkt 1

HCID 569706444-(1-Phenylcyclopropylamino)-6-(4-(4-propionylpiperazin-1-yl)phenylamino)nicotinamideAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 6-chloro-4-(1-phenylcyclopropylamino)nicotinamide (50 mg, 0.174 mmol) in dioxane (1 mL) was added 1-(4-(4-aminophenyl)piperazin-1-yl)propan-1-one (61 mg, 0.261 mmol), BINAP (22 mg, 0.035 mmol), Pd(OAc)2 (8 mg, 0.035 mmol) and Cs2CO3 (170 mg, 0.52 mmol). After degassed with Argon, the mixture was heated at 80° C. for 15 h. The mixture was diluted with dioxane, precipitate was filtered off, filter cake was washed with AcCN, the filtrate was concentrated and purified by preparative HPLC to give of 4-(1-phenylcyclopropylamino)-6-(4-(4-propionylpiperazin-1-yl)phenylamino)nicotinamide (16 mg). MS found for C28H32N6O2 as (M+H)+ 485.5. λ=258.2.

Aufarbeitung

  1. customAfter degassed with Argon
  2. additionThe mixture was diluted with dioxane, precipitate
  3. filtrationwas filtered off
  4. filtrationfilter cake
  5. washwas washed with AcCN
  6. concentrationthe filtrate was concentrated
  7. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cb4b8f6e590c4cc29ddb94d837a7f46b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102625B2

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