Diisopropylethylamine → HCID 86714421, Verbindung

HRID 1750210

Reaktionsgleichung

Reaktionsgleichung von HRID 1750210
[S:1]1[C:5]([CH2:6][C:7]([OH:9])=O)=[CH:4][N:3]=[CH: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>O.C(Cl)CCl.CN(C=O)C>[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[S:1][CH:2]=[N:3][CH:4]=2)[CH:33]=1

Komponenten

8

Edukt 4

HCID 81531Diisopropylethylamine2×HCID 181649HOAtHCID 3494395-Thiazoleacetic acidHCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Produkt 1

HCID 86714421HCID 86714421, VerbindungAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g of Thiazol-5-yl-acetic acid in 17 nil of dry DMF 0.48 g of HOAT, 1.61 g of EDC and 2.3 ml of DIPEA were added at 0° C. After 30 min 1.65 g of 3-Amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester were added, followed by the addition of 2 ml of DIPEA and the reaction was stirred at it for 48 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 to obtain 2.16 g (85%) of 4-(1-Ethyl-propylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester, which was used without further purification.

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

Quellen und Nachweise

ORD-Eintrag
ord-020405a5462942888d9e9ae400e6b484
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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