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Acetic Acid → 2-{[3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzamide

HRID 915595
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 915595
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[N:3]=1.Br[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:16]2[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=2[C:18]([NH2:20])=[O:19])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 776162-BromobenzamideHCID 7756883-Methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine2×

Produkt 1

HCID 100408062-{[3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzamideAusbeute 21,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895
Cupric acetate
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate F, 1.00 g, 5.3 mmol), 2-bromobenzamide (1.07 g, 5.3 mmol), potassium carbonate (0.89 g, 6.4 mmol), and copper (II) acetate (39 mg, 0.2 mmol) in DMF (20 mL) was heated (150° C.) in a sealed tube for 18 h. After cooling, the solution was adjusted to pH=4 using glacial acetic acid. The reaction mixture was extracted with dichloromethane (3×20 mL), and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 33-50% ethyl acetate/hexane afforded a yellow solid that was washed with diethyl ether to give 2-{[3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzamide (350 mg, 21%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 10.48 (s, 1H), 8.01 (s, 1H), 7.67 (dd, 1H), 7.32 (m, 7H), 6.77 (ddd, 1H), 6.08 (s, 1H), 2.19 (s, 3H), 2.00 (s, 3H); ES-MS m/z 307.1 (MH+); HPLC RT (min) 2.41.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe reaction mixture was extracted with dichloromethane (3×20 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customFlash chromatography of the residue over silica gel using 33-50% ethyl acetate/hexane afforded a yellow solid
  8. washthat was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c35eb3343acc4f668b2a134797d2e5b3
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07265144B2

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