1-Hydroxybenzotriazole → HCID 86714418, Verbindung

HRID 1750207

Reaktionsgleichung

Reaktionsgleichung von HRID 1750207
[Cl:1][C:2]1[S:6][C:5]([CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:30][O:31][C:32](=[O:46])[C:33]1[CH:38]=[CH:37][C:36]([NH:39][CH:40]([CH2:43][CH3:44])[CH2:41][CH3:42])=[C:35]([NH2:45])[CH:34]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:30][O:31][C:32](=[O:46])[C:33]1[CH:38]=[CH:37][C:36]([NH:39][CH:40]([CH2:41][CH3:42])[CH2:43][CH3:44])=[C:35]([NH:45][C:8](=[O:10])[CH2:7][C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:34]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 44267162-(5-chlorothiophen-2-yl)acetic AcidHCID 61311526HCID 61311526, Verbindung

Produkt 1

HCID 86714418HCID 86714418, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g of 5-Chlorothiophen-2-yl-acetic acid in 15 ml of dry DMF 0.84 g of HOBT, 1.19 g of EDC and 1.5 ml of DIPEA were added at 0° C. After 30 min 1.33 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 1.5 ml of DIPEA were added and the reaction was stirred at rt 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 crystallization from diethylether to yield 2.00 g (89%) of 3-[2-(5-Chloro-thiophen-2-yl)-acetylamino]-4-(1-ethyl-propylamino)-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 crystallization from diethylether

Quellen und Nachweise

ORD-Eintrag
ord-bd67a932963d4c55a2a26753a700da1d
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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