Phenylacetic Acid → N-benzyl-2-(5-benzyl-1,2,4-oxadiazol-3-yl)-4-methylthiazole-5-carboxamide

HRID 2381869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381869
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38](=[N:40]O)[NH2:39])=[N:35][C:34]=1[CH3:42])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.ClCCl>[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38]2[N:40]=[C:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:10][N:39]=2)=[N:35][C:34]=1[CH3:42])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 999Phenylacetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 136404881N-benzyl-2-(N'-hydroxycarbamimidoyl)-4-methylthiazole-5-carboxamide

Produkt 1

HCID 59179717N-benzyl-2-(5-benzyl-1,2,4-oxadiazol-3-yl)-4-methylthiazole-5-carboxamideAusbeute 6,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of phenylacetic acid (0.05 g, 0.37 mmol) in N,N-dimethylformamide (2 mL) was added 1,1′-carbonyldiimidazole (0.14 g, 0.83 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, and N-benzyl-2-(N′-hydroxy-carbamimidoyl)-4-methylthiazole-5-carboxamide (0.12 g, 0.41 mmol) was added. The reaction mixture was stirred for 17 hours, diluted with dichloromethane, washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white powder (0.01 g, 6%): mp 124-125° C.; 1H NMR (300 MHz, CDCl3) δ 7.45-7.25 (m, 10H), 6.16 (t, J=5.6 Hz, 1H), 4.60 (d, J=5.6 Hz, 2H), 4.29 (s, 2H), 2.76 (s, 3H); MS (ES+) m/z 391.5 (M+1).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 17 hours
  2. washwashed with water and brine
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-618c7a85116e4dff9ed9c208b974e253
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258160B2

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