Triethylamine → (E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-but-3-enenitrile

HRID 660754

Reaktionsgleichung

Reaktionsgleichung von HRID 660754
[CH3:1][CH:2]([CH:5]=[CH2:6])[C:3]#[N:4].[CH2:7]([O:14][C:15]1[CH:20]=[C:19](I)[CH:18]=[CH:17][C:16]=1[N:22]1[S:26](=[O:28])(=[O:27])[NH:25][C:24](=[O:29])[CH2:23]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:7]([O:14][C:15]1[CH:20]=[C:19](/[CH:6]=[CH:5]/[CH:2]([CH3:1])[C:3]#[N:4])[CH:18]=[CH:17][C:16]=1[N:22]1[CH2:23][C:24](=[O:29])[NH:25][S:26]1(=[O:28])=[O:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 279092-Methyl-3-butenenitrileHCID 688386435-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Produkt 1

HCID 68839915(E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-but-3-enenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 2-methyl-but-3-enenitrile (18 mg, 0.225 mmol), 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (50 mg, 0.113 mmol), Pd(OAc)2 (5 mg, 0.023 mmol) and triethylamine (11 mg, 0.107 mmol) in THF (3 mL) is placed in a microwave vial and heated at 110° C. for 10 min. The mixture is filtered and the filtrate concentrated. The residue is purified by reverse phase HPLC to give the title compound.

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue is purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-14f89c40c83145309f7346db4efbc780
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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