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1-Hydroxybenzotriazole → 8-Hydroxy-N-methyl-N-(4-(2-phenylpropan-2-yl)benzyl)quinoline-2-carboxamide

HRID 1025542
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1025542
CCN=C=N[CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].Cl.C1C=CC2N([OH:22])N=NC=2C=1.CNCC1[CH:31]=[CH:30][C:29]([C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([CH3:34])[CH3:33])=[CH:28]C=1.[OH:41][C:42]1[C:43](C(O)=O)=[CH:44][CH:45]=[C:46]2[C:51]=1[N:50]=[CH:49][CH:48]=[CH:47]2>C(Cl)Cl>[OH:41][C:42]1[CH:43]=[CH:44][CH:45]=[C:46]2[C:51]=1[N:50]=[C:49]([C:11]([N:9]([CH3:10])[CH2:8][C:7]1[CH:6]=[CH:28][C:29]([C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)([CH3:33])[CH3:34])=[CH:30][CH:31]=1)=[O:22])[CH:48]=[CH:47]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18333891N-[4-(1-Methyl-1-phenylethyl)benzyl]-methylamine

Produkt 1

HCID 672931388-Hydroxy-N-methyl-N-(4-(2-phenylpropan-2-yl)benzyl)quinoline-2-carboxamide
Ausbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TEA (42 mg, 0.42 mmol), EDC.HCl (80 mg, 0.42 mmol), HOBt (57 mg, 0.418 mmol) and N-methyl-1-(4-(2-phenylpropan-2-yl)phenyl)methanamine (50 mg, 0.21 mmol) of Preparation 1 were sequentially added to a suspension of 8-hydroxyquinoline-7-carboxylic acid (48 mg, 0.25 mmol) in DCM (2.5 mL). The resulting reaction mixture was stirred at RT overnight. The mixture was quenched with H2O and then extracted three times with DCM. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, DCM:MeOH 95:5) affording the title compound (39 mg, 0.1 mmol) as a grey solid. LC-MS m/z (ESI+): 411.2 (MH+), Rt=2.42 min (Method A).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe mixture was quenched with H2O
  3. extractionextracted three times with DCM
  4. dry with materialThe separated organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, DCM:MeOH 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-2f4323f60f0343f0b75e2947b552144f
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729098B2

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