1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-[3-(1H-indol-4-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

HRID 423329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423329
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([OH:8])=O)#[N:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O[NH:38][C:39]([C:41]1[C:42]2[CH:43]=[CH:44][NH:45][C:46]=2[CH:47]=[CH:48][CH:49]=1)=[NH:40]>CN(C=O)C.CCOC(C)=O>[NH:45]1[C:46]2[C:42](=[C:41]([C:39]3[N:38]=[C:6]([C:5]4[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[C:3]([CH:4]=4)[C:1]#[N:2])[O:8][N:40]=3)[CH:49]=[CH:48][CH:47]=2)[CH:43]=[CH:44]1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide3×HCID 757711-Hydroxybenzotriazole3×HCID 21956832RP-101124HCID 178513279HCID 178513279, Verbindung

Produkt 1

HCID 593183965-[3-(1H-indol-4-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrileAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (500 mg, 2.44 mmol) in DMF (15 ml) was added EDAC (514 mg, 2.67 mmol) and HOBt (367 mg, 2.67 mmol) and the solution left standing for 30 minutes. Added N-hydroxy-1H-indole-4-carboximidamide (D9) (427 mg, 2.44 mmol) and left standing for 1 hour. To the solution were added EDAC (117 mg, 0.61 mmol) and HOBt (84 mg, 0.61 mmol) and left standing for 2 hours. To the solution were added EDAC (234.9 mg, 1.22 mmol) and HOBt (167.7 mg, 1.22 mmol) and left standing overnight. Heated at 80° C. overnight, cooled and added EtOAc (30 ml). Washed with water (30 ml), sat. sodium hydrogen carbonate (30 ml) and water (30 ml). Dried over MgSO4 and evaporated off the solvent. The residue was triturated with diethyl ether to give 353 mg of the title compound as a pale brown solid. δH (400 MHz, d6-DMSO) 1.39 (6H, d), 4.94-5.03 (1H, m), 7.09-7.10 (1H, m), 7.30 (1H, t), 7.56-7.59 (2H, m), 7.67 (1H, d), 7.92 (1H, dd), 8.45 (1H, dd), 8.55 (1H, d), 11.52 (1H, broad s). MS (ES) C20H16N4O2 requires 344; found 345 (MH+).

Aufarbeitung

  1. waitthe solution left
  2. waitstanding for 1 hour
  3. waitleft
  4. waitstanding for 2 hours
  5. waitleft
  6. waitstanding overnight
  7. temperaturecooled
  8. washWashed with water (30 ml), sat. sodium hydrogen carbonate (30 ml) and water (30 ml)
  9. dry with materialDried over MgSO4
  10. customevaporated off the solvent
  11. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-48d1994ba6d74a76aef1e37c3575034b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101775B2

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