Phenylpropiolic Acid → HCID 68816767, Verbindung

HRID 735036

Reaktionsgleichung

Reaktionsgleichung von HRID 735036
[C:1]1([C:7]#[C:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12]([N:14]([CH2:26][CH3:27])[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1)[CH3:13].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[CH2:26]([N:14]([CH2:12][CH3:13])[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][NH:25][C:9](=[O:11])[C:8]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:22][CH:23]=1)[CH3:27]

Komponenten

8

Edukt 5

HCID 69475Phenylpropiolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 235944{4-[2-(Diethylamino)ethoxy]phenyl}methanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 68816767HCID 68816767, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 0.29 g (2 mmol) of phenylpropynoic acid, 0.44 g (2 mmol) of [4-(2-diethylaminoethoxy)phenyl]methylamine, 0.7 g (2.2 mmol) of TBTU, 0.29 g (2.2 mmol) of HOBT and 0.51 mL (3 mmol) of Hünig base in 30 mL of THF and 2 mL of DMF is stirred for 14 hours at ambient temperature. The reaction mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol (80:20)). Yield: 130 mg (18.5% of theory); C22H26N2O2 (M=350.46); calc.: molecular ion peak (M+H)+: 351; found: molecular ion peak (M+H)+: 351; Rf value: 0.39 (silica gel, dichloromethane/methanol (80:20)).

Aufarbeitung

  1. customThe reaction mixture is evaporated down
  2. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-d8977cacbe1e46ffbd03041c4a886eb2
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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