Triethylamine → HCID 178425195, Verbindung

HRID 1501005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1501005
[CH3:1][C:2]1[CH:10]=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.[NH2:26][CH2:27][C:28]1[C:29]([OH:36])=[N:30][C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34]>ClCCl>[OH:36][C:29]1[C:28]([CH2:27][NH:26][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:2]=2[CH3:1])=[C:33]([CH3:34])[CH:32]=[C:31]([CH3:35])[N:30]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 67601994Methyl 4-(phenoxymethyl)benzoic acidHCID 178425242HCID 178425242, Verbindung

Produkt 1

HCID 178425195HCID 178425195, VerbindungAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-Methyl-4-(phenoxymethyl)benzoic acid (42 mg, 0.17 mmol), o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyfluoroniumhexafluorophosphate (99 mg, 0.26 mmol), triethylamine (0.1 mL) and dichloromethane (15 mL) were stirred at 25° C. for half hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (27 mg, 0.17 mmol) was added to the mixture. The mixture was stirred at 25° C. for 12 hours. The resultant mixture was washed with water (20 mL), dried over sodium, filtered, and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-4-(phenoxymethyl)benzamide as a white solid (50 mg, 78%). LRMS (M+H+) m/z: calcd 376.18. found 376. HPLC purity (214 nm): 98%. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.11 (t, J=4.8 Hz, 1H), 7.28-7.20 (m, 5H), 7.00-6.84 (m, 3H), 5.86 (s, 1H), 5.07 (s, 2H), 4.27 (d, J=4.8 Hz, 2H), 2.31 (s, 3H), 2.19 (s, 3H), 2.11 (s, 3H).

Aufarbeitung

  1. washThe resultant mixture was washed with water (20 mL)
  2. dry with materialdried over sodium
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-777f47683c724d1db3030970defc1cf7
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206128B2

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