Triethylamine → N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)benzamide

HRID 736387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736387
[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([NH:25][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)=[CH:16][CH:15]=2)=[CH:26][CH:27]=1)([CH3:20])([CH3:18])[CH3:19]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 698614-Tert-ButylanilineHCID 757711-HydroxybenzotriazoleHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Produkt 1

HCID 11451387N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

The product from Example 24A (75.0 mg, 0.321 mmol), 4-tert-butylaniline (61 μL, 0.383 mmol), PS-DCC (1.35 mmol/g, 0.7132 g, 0.963 mmol), HOBT (44.0 mg, 0.326 mmol), and triethylamine (0.13 mL, 0.93 mmol) in DMF (3 mL) were combined and heated at 55° C. for 16 hours. The mixture was allowed to cool to room temperature, filtered, and the filtrate was diluted with diethyl ether (20 mL). The diethyl ether was washed with 1N HCl (15 mL), brine (15 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.63 (dd, 1H), 7.98 (d, 2H), 7.88 (d, 2H), 7.83 (d, 1H), 7.81 (br s, 1H), 7.59 (d, 2H), 7.41 (d, 2H), 7.29 (dd, 1H), 1.33 (s, 9H); MS (m/z) 365.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. additionthe filtrate was diluted with diethyl ether (20 mL)
  4. washThe diethyl ether was washed with 1N HCl (15 mL), brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3c86b291d7c048f2af1cc1022990583a
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595332B2

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