Sodium Carbonate → HCID 178428276, Verbindung

HRID 16198

Reaktionsgleichung

Reaktionsgleichung von HRID 16198
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])=[CH:11][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[NH2:21][C:22]1[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(OCC)(=O)C.O>[CH3:27][C:25]1[CH:26]=[C:22]([NH:21][C:2]2[N:7]=[C:6]([S:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])=[CH:11][CH:10]=3)[CH:5]=[N:4][CH:3]=2)[NH:23][N:24]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59343401N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide

Produkt 1

HCID 178428276HCID 178428276, VerbindungAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide (0.49 mmol) and 3-amino-5-methylpyrazole (0.52 mmol) in 1,4-dioxan (3 mL), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.03 mmol), tris(dibenzylideneacetone) dipalladium (0.02 mmol) and sodium carbonate (0.69 mmol) were added. The resulting solution was heated at 120° C. in the microwave (175 W, 25 psi) for 30 min. Water (10 mL) and ethyl acetate (10 mL) were added and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×10 mL), the combined organic layers dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/Petroleum ether, 0-100% gradient EtOAc) and then purified further using mass directed HPLC purification (sunfire C18 column, trifluoroacetic acid/MeCN/MeOH as eluent) to give the title compound (10.6 mg, 6%) as a light yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 0.81 (4H, m), 1.83 (1H, m), 2.05 (3H, s), 5.55 (1H, s), 7.54 (2H, m), 7.59 (1H, s), 7.74 (2H, m), 8.02 (1H, s), 9.77 (1H, s), 10.47 (1H, s); MS (ES+): m/e=367.41 (100%).

Aufarbeitung

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with ethyl acetate (2×10 mL)
  3. dry with materialthe combined organic layers dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (EtOAc/Petroleum ether, 0-100% gradient EtOAc)
  6. custompurified further
  7. customHPLC purification (sunfire C18 column, trifluoroacetic acid/MeCN/MeOH as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-5901f94139ab4943bf677c4ac808e903
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737151B2

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