Acetic Acid → 5-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino]benzoic acid

HRID 915593

Reaktionsgleichung

Reaktionsgleichung von HRID 915593
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH2:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[CH:22][CH:21]=1.C(O)(=O)C>CN(C=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:2]([NH:19][C:20]2[N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:23]=[CH:22][CH:21]=2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 700061-Phenylpyrazol-5-ylamineHCID 899062-Bromo-5-methoxybenzoic acid

Produkt 1

HCID 589586195-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino]benzoic acidAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-bromo-5-methoxy benzoic acid (1.31 g, 5.7 mmol), potassium carbonate (859 mg, 6.2 mmol), 5-amino-1-phenyl-pyrazole (900 mg, 5.7 mmol), and copper (II) acetate (21 mg, 0.11 mmol) in DMF (12 mL) was heated (150° C.) in a sealed tube for 16 h. After cooling, the reaction mixture was diluted with water (5 mL), and then acidified to pH 4 with acetic acid. The mixture was extracted with dichloromethane (3×10 mL), and then the combined organic extracts were washed with water (2×10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. HPLC purification of the residue (YMC propack C18 column, 150×20 mm ID, 30%-80% acetonitrile in water gradient) afforded 5-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino] benzoic acid (450 mg, 26%) as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 13.33 (br s, 1H), 9.62 (br s, 1H), 7.64 (d, 1H), 7.34-7.58 (m, 6H), 7.00-7.11 (m, 2H), 6.30 (d, 1H), 3.69 (s, 3H); ES-MS m/z 310.1 (MH+); HPLC RT (min) 2.74.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  3. washthe combined organic extracts were washed with water (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customHPLC purification of the residue (YMC propack C18 column, 150×20 mm ID, 30%-80% acetonitrile in water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d538756134754c49ad666faf101b821f
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265144B2

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