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Sodium Bicarbonate → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-{6-[(methylamino)sulfonyl]-3-pyridinyl}-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 476025
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 476025
Br[C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[N:6][CH:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Cl[C:37]1[CH:38]=[C:39]([C:49]([NH:51][CH2:52][C:53]2[C:54](=[O:61])[NH:55][C:56]([CH3:60])=[CH:57][C:58]=2[CH3:59])=[O:50])[C:40]2[CH:45]=[N:44][N:43]([CH:46]([CH3:48])[CH3:47])[C:41]=2[N:42]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.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.O.COCCOC>[CH3:59][C:58]1[CH:57]=[C:56]([CH3:60])[NH:55][C:54](=[O:61])[C:53]=1[CH2:52][NH:51][C:49]([C:39]1[C:40]2[CH:45]=[N:44][N:43]([CH:46]([CH3:48])[CH3:47])[C:41]=2[N:42]=[C:37]([C:2]2[CH:7]=[N:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:38]=1)=[O:50]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 5

HCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamideHCID 584364765-Bromo-N-methyl-2-pyridinesulfonamide

Produkt 1

HCID 56598940
N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-{6-[(methylamino)sulfonyl]-3-pyridinyl}-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-Bromo-N-methyl-2-pyridinesulfonamide (225 mg, 0.896 mmol), Bis(pinacolato)diboron (296 mg, 1.165 mmol), Pd(dppf) (35.7 mg, 0.044 mmol) and potassium acetate (264 mg, 2.69 mmol) were suspended in 1,4-Dioxane (8 mL), and stirred with heating at 100° C. for 1 h. After cooling to room temperature, 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (368 mg, 0.986 mmol), bis(triphenylphosphine)palladium(II) chloride (73.2 mg, 0.090 mmol) and sodium bicarbonate (226 mg, 2.69 mmol) were added, followed by DME (5 mL) and water (3 mL). The reaction mixture was irradiated (microwave) at 120° C. for 2 h. The reaction mixture was cooled cooled to room temperature and filtered through Na2SO4. The contents were purified directly by silica gel chromatography (eluent: 15% MeOH/CH2Cl2) to furnish the desired product as a grey solid after evaporation and precipitation from warm EtOAc/MeOH (1:9). The product was again purified by silica gel chromatography (eluent: 5% MeOH/CH2Cl2) to afford the final product as a white solid, 83 mg (18%). LCMS E-S (M+H)=510.0 1H NMR (400 MHz, DMSO-d6) δ ppm 11.59 (br. s., 1H), 9.56 (d, J=1.52 Hz, 1H), 8.96 (s, 1H), 8.86 (dd, J=8.34, 2.27 Hz, 1H), 8.46 (s, 1H), 8.34 (s, 1H), 8.12 (d, J=8.34 Hz, 1H), 7.85 (br. s., 1H), 5.91 (s, 1H), 5.27-5.46 (m, 1H), 4.43 (d, J=4.80 Hz, 2H), 2.60 (s, 3H), 2.23 (s, 3H), 2.13 (s, 3H), 1.56 (d, 6H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customThe reaction mixture was irradiated (microwave) at 120° C. for 2 h
  3. temperatureThe reaction mixture was cooled
  4. temperaturecooled to room temperature
  5. filtrationfiltered through Na2SO4
  6. customThe contents were purified directly by silica gel chromatography (eluent: 15% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-0861d42036b74b73be776001cdd62138
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08637509B2

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