Cesium carbonate → 5'-Methoxy-N,2'-dimethyl-4'-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)biphenyl-4-carboxamide

HRID 2091952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091952
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH3:30])=[O:28])=[CH:23][CH:22]=3)=[C:15]([CH3:31])[CH:14]=2)[N:3]=1.[CH3:32][C:33]1[NH:37][N:36]=[C:35]([NH2:38])[CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][O:19][C:18]1[C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:38][C:35]3[CH:34]=[C:33]([CH3:32])[NH:37][N:36]=3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][C:15]([CH3:31])=[C:16]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH3:30])=[O:28])=[CH:23][CH:22]=2)[CH:17]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 866477934'-(4-Chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

Produkt 1

HCID 252654055'-Methoxy-N,2'-dimethyl-4'-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)biphenyl-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

The mixture of 4′-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-5′-methoxy-N,2′-dimethylbiphenyl-4-carboxamide (Step 1, 20 mg, 0.044 mmol), 5-methyl-1H-pyrazol-3-amine (4.3 mg, 0.044 mmol), Xantophos (5.0 mg, 0.009 mmol), paladium acetate (II) (1.0 mg, 0.004 mmol), and cesium carbonate (28.6 mg, 0.088 mmol) in 2.0 mL of THF is heated at 150° C. in a microwave reactor for 25 min. The reaction mixture is filtered, the filtrate is concentrated in vacuo, and purified by preparative RP-HPLC to afford 5′-Methoxy-N,2′-dimethyl-4′-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)biphenyl-4-carboxamide; ESMS m/z 512.2 (M+H+).

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. custompurified by preparative RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d742f89beaf64013b725ebc242cc6066
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440681B2

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