Dimethylformamide → 5-Methyl-N-{5-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyrazin-2-yl}-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748665
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[C:15]=2[CH3:16])=[O:10])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH2:40][CH2:39][CH:38]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH2:37][CH:36]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O1CCOCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:16][C:15]1[N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)[N:13]=[CH:12][C:11]=1[C:9]([NH:8][C:5]1[CH:4]=[N:3][C:2]([C:35]2[CH2:40][CH2:39][CH:38]([N:41]3[CH2:42][CH2:43][O:44][CH2:45][CH2:46]3)[CH2:37][CH:36]=2)=[CH:7][N:6]=1)=[O:10]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 592386904-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)morpholineHCID 86692610N-(5-bromopyrazin-2-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Produkt 1

HCID 866926095-Methyl-N-{5-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyrazin-2-yl}-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamideAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178419050HCID 178419050, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of N-(5-bromopyrazin-2-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (300 mg), 4-[4-(4,4,5,5-tetramethyl[1,3,2] dioxaborolan-2-yl)cyclohex-3-en-1-yl]morpholin (185 mg), tetrakis(trophenylphosphine)palladium (0) (81 mg) and sodium carbonate (186 mg) in 1,4-dioxane (7.0 ml) was stirred at 90° C. for four hours. Then, N,N-dimethylformamide (7.0 ml) and bis(diphenylphosphine)ferrocenepalladium (II) dichloride dichloromethane adduct (57 mg) were added at room temperature and stirred at 90° C. for five hours. After completion of the reaction, the reaction solution was cooled to room temperature, water was added, and the precipitated solid was collected by filtration. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) twice to give the titled compound (143 mg) as a white solid.

Aufarbeitung

  1. stirringstirred at 90° C. for five hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled to room temperature
  4. filtrationthe precipitated solid was collected by filtration
  5. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol) twice

Quellen und Nachweise

ORD-Eintrag
ord-a7ac70f53baf4ac9a4506db65c9e35ed
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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