Lithium methanolate → 4-{3E-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzamide

HRID 10715

Reaktionsgleichung

Reaktionsgleichung von HRID 10715
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[N:13]1([CH2:19][CH2:20][O:21][C:22]2[CH:29]=[C:28]([O:30][CH3:31])[C:27]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[CH:26][C:23]=2[CH:24]=O)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C[O-].[Li+]>CN(C=O)C.CO>[CH3:31][O:30][C:28]1[C:27]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)=[CH:26][C:23](/[CH:24]=[CH:2]/[C:1]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=2)=[O:3])=[C:22]([O:21][CH2:20][CH2:19][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:29]=1

Komponenten

6

Edukt 3

HCID 4177230Lithium methanolateHCID 111594974-AcetylbenzamideHCID 161161844-Methoxy-2-(2-morpholin-4-ylethoxy)-5-thien-2-ylbenzaldehyde

Produkt 1

HCID 103909574-{3E-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzamideAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-acetyl-benzamide (Ex-92A, 0.25 g, 1.53 mmol) and 2-(2-morpholin-4-yl-ethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-60A, 0.53 g, 1.53 mmol) in DMF (7 mL) and methanol (3 mL) was added lithium methoxide. The solution was allowed to stir at ambient temperature. The reaction was quenched with water after 2 hours. The aqueous solution was extracted with ethyl acetate. The combined extract was washed with NaHCO3, NH4Cl, brine, dried (Na2SO4) and concentrated. The residue was stirred in ethanol overnight to afford the title compound as a yellow solid (0.43 g, 57%), mp 183–184° C. 1H-NMR (CDCl3) δ 8.09–8.04 (m, 3H), 7.93 (d, J=8.3 Hz, 2H), 7.87 (s, 1H), 7.57 (d, J=15.7 Hz, 1H), 7.42 (d, J=3.9 Hz, 1H), 7.32 (d, 4.4 Hz, 1H), 7.11–7.08 (m, 1H), 6.55 (s, 1H), 6.25 (bs, 1H), 5.75 (bs, 1H), 4.25 (t, J=5.9 Hz, 2H), 3.98 (s, 3H), 3.71 (t, J=4.2 Hz, 4H), 2.92 (t, J=5.7 Hz, 2H), 2.59 (t, J=4.6 Hz, 4H). MS m/z=493 ([M+H]+, 100%).

Aufarbeitung

  1. customThe reaction was quenched with water after 2 hours
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with NaHCO3, NH4Cl, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. stirringThe residue was stirred in ethanol overnight

Quellen und Nachweise

ORD-Eintrag
ord-65a52f3bb4944230af47e3a45db65550
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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