Acetic Acid → 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid

HRID 915580

Reaktionsgleichung

Reaktionsgleichung von HRID 915580
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:19]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:20]=1[C:21]([OH:23])=[O:22].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:19]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:20]=2[C:21]([OH:23])=[O:22])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 899062-Bromo-5-methoxybenzoic acidHCID 7706433-tert-Butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine2×

Produkt 1

HCID 100682862-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acidAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate C, 1.00 g, 4.36 mmol) in DMF (20 mL), was added 2-bromo-5-methoxybenzoic acid (1.01 g, 4.36 mmol), potassium carbonate (723 mg, 5.23 mmol), and copper (II) acetate (32 mg, 0.17 mmol). The mixture was stirred at 150° C. for 18 h and then cooled to rt. The solution was adjusted to pH 4 using glacial acetic acid. The mixture was extracted with dichloromethane (3×5 mL), and then the combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by HPLC (45-90% acetonitrile in water) to afford the product (500 mg, 33%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (s, 9H), 1.98 (s, 3H), 3.69 (s, 3H), 6.19 (s, 1H), 7.14 (dd, 1H), 7.26-7.37 (m, 6H), 9.49 (s, 1H), 13.25 (s, 1H); ES-MS m/z 380.3 (MH+); HPLC RT (min) 3.18.

Aufarbeitung

  1. temperaturecooled to rt
  2. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by HPLC (45-90% acetonitrile in water)

Quellen und Nachweise

ORD-Eintrag
ord-244bbe80b19045e991aa7a7198ac5752
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265144B2

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