Diisopropylethylamine → HCID 86714425, Verbindung

HRID 1750214

Reaktionsgleichung

Reaktionsgleichung von HRID 1750214
[O:1]1[C:5]([CH2:6][C:7]([OH:9])=O)=[CH:4][CH:3]=[N:2]1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[C:34]([NH2:44])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:40][CH3:41])[CH2:42][CH3:43])=[C:34]([NH:44][C:7](=[O:9])[CH2:6][C:5]2[O:1][N:2]=[CH:3][CH:4]=2)[CH:33]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 13042084isoxazol-5-yl-acetic acidHCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Produkt 1

HCID 86714425HCID 86714425, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.71 g of Isoxazol-5-yl-acetic acid in 15 ml of dry DMF 0.38 g of HOAT, 1.29 g of EDC and 3 ml of DIPEA were added at 0° C. After 30 min 1.32 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester were added and the reaction was stirred at it for 16 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by precipitation from diisoprpylether to yield 1.06 g (55%) of 4-(1-Ethyl-propylamino)-3-(2-isoxazol-5-yl-acetylamino)-benzoic acid methyl ester.

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by precipitation from diisoprpylether

Quellen und Nachweise

ORD-Eintrag
ord-4f8d2823a07a477a86bd754f8de1385b
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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