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Dimethylformamide → N-[(4-chlorophenyl)methyl]-1-methyl-8-[3-(5-methylimidazol-1-yl)prop-1-ynyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 2086619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2086619
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14](I)[CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH3:29])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Br.[CH3:33][C:34]1[N:38]([CH2:39][C:40]#[CH:41])[CH:37]=[N:36][CH:35]=1.CN(C=O)C>N(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([C:41]#[C:40][CH2:39][N:38]4[C:34]([CH3:33])=[CH:35][N:36]=[CH:37]4)[CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH3:29])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1
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Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 12095879N-(4-chlorobenzyl)-8-iodo-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamideHCID 227245555-methyl-1-prop-2-ynyl-1H-imidazole hydrobromide

Produkt 1

HCID 5278419N-[(4-chlorophenyl)methyl]-1-methyl-8-[3-(5-methylimidazol-1-yl)prop-1-ynyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamideAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

To a solution of N-(4-chlorobenzyl)-8-iodo-1-methyl-6-(morpholin-4-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (300 mg), PdCl2(PPh3)2 (19.1 mg), and CuI (5.2 mg) in Et2NH (6.2 mL) is added 5-methyl-1-prop-2-ynyl-1H-imidazole hydrobromide (120.4 mg). Anhydrous DMF (10 mL) is added to help solubilize the reactants (also requires sonication). The reaction is stirred at room temperature overnight, then condensed. The resulting residue is placed under high vacuum to remove residual DMF. The crude product is dissolved in CH2Cl2 and partitioned between CH2Cl2 and saturated NaHCO3. The layers are separated. The aqueous layer is extracted with CH2Cl2 (2×). The combined organic layers are dried over Na2SO4, filtered, and condensed. The crude product is adsorbed onto silica and chromatographed (eluant 1% MeOH in CH2Cl2 (1L), 2% MeOH in CH2Cl2 (1L), 3% MeOH in CH2Cl2 (1L), 4% MeOH in CH2Cl2 (2L), and 6% MeOH in CH2Cl2 (1L)). Product-containing fractions are combined and concentrated to afford a residue. The residue is recrystallized from hot acetonitrile to afford 87.7 mg of the title compound as a tan solid.

Aufarbeitung

  1. customalso requires sonication)
  2. customcondensed
  3. customto remove residual DMF
  4. dissolutionThe crude product is dissolved in CH2Cl2
  5. custompartitioned between CH2Cl2 and saturated NaHCO3
  6. customThe layers are separated
  7. extractionThe aqueous layer is extracted with CH2Cl2 (2×)
  8. dry with materialThe combined organic layers are dried over Na2SO4
  9. filtrationfiltered
  10. customcondensed
  11. customchromatographed (eluant 1% MeOH in CH2Cl2 (1L), 2% MeOH in CH2Cl2 (1L), 3% MeOH in CH2Cl2 (1L), 4% MeOH in CH2Cl2 (2L), and 6% MeOH in CH2Cl2 (1L))
  12. concentrationconcentrated
  13. customto afford a residue
  14. customThe residue is recrystallized from hot acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-eb79627e10524abd860b44641d0da6b0
Quelldatensatz
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06727248B2

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