Isopropyl iodide → HCID 58958570, Verbindung

HRID 915594

Reaktionsgleichung

Reaktionsgleichung von HRID 915594
C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:8]([CH3:10])[CH3:9].[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:22][C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][CH:24]=2)=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19]>CN(C=O)C>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:22][C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][CH:24]=2)=[C:17]([CH:21]=1)[C:18]([O:20][CH:8]([CH3:10])[CH3:9])=[O:19]

Komponenten

5

Edukt 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 589586195-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino]benzoic acid

Produkt 1

HCID 58958570HCID 58958570, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Cesium carbonate (105 mg, 0.19 mmol) and 2-iodopropane (18 mg, 0.11 mmol) were added to a solution of the intermediate 5-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino] benzoic acid (30 mg, 0.10 mmol) in DMF (4 mL). The mixture was stirred at rt for 16 h. The reaction was quenched with water (5 mL) and then extracted with dichloromethane (3×5 mL). The combined organic layers were washed with water (5 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 the desired product as a white solid (20 mg, 59%). 1H NMR (300 MHz, DMSO-d6) δ 9.07 (s, 1H), 7.65 (d, 1H), 6.96-7.56 (m, 9H), 6.29 (dd, 1H), 5.06 (q, 1H), 3.69 (s, 3H), 1.24 (d, 6H); ES-MS m/z 352.1 (MH+); HPLC RT (min) 3.53.

Aufarbeitung

  1. customThe reaction was quenched with water (5 mL)
  2. extractionextracted with dichloromethane (3×5 mL)
  3. washThe combined organic layers were washed with water (5 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-fe82ba2049a54c6dbf039174a4f840cf
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265144B2

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