1-Hydroxybenzotriazole → HCID 86714415, Verbindung

HRID 1750203

Reaktionsgleichung

Reaktionsgleichung von HRID 1750203
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.C1C=CC2N(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:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:33]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 75974Furan-2-acetic acidHCID 81531Diisopropylethylamine2×HCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Produkt 1

HCID 86714415HCID 86714415, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4.48 g of 2-furylacetic acid in 30 ml of dry DMF 1.00 g of HOBT, 3.97 g of EDC and 1.8 ml of DIPEA were added at 0° C. After 30 min 3.50 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 1.8 ml of DIPEA 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 carbonate solution and saturated aqueous ammonium chloride solution, dried over magnesium sulphate and concentrated to obtain 4.44 g (87%) of 4-(1-Ethyl-propylamino)-3-(2-furan-2-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 carbonate solution and saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c5b41ad70ccd4455b9fef9362a942927
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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