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Dichloromethane → 6-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(lH)-quinolinone

HRID 704636
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 704636
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[C:21]([CH:28]=[CH:29][C:30](OCC)=[O:31])[C:22]([N+:25]([O-])=O)=[CH:23][CH:24]=4)[CH2:15][CH2:14]3)=[O:12])[N:10]=[C:4]2[CH:3]=1.ClCCl.[H][H]>[C].[Pd].CO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[C:21]5[C:22](=[CH:23][CH:24]=4)[NH:25][C:30](=[O:31])[CH2:29][CH2:28]5)[CH2:15][CH2:14]3)=[O:12])[N:10]=[C:4]2[CH:3]=1
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Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 54465980Ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 200727986-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(lH)-quinolinoneAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390
HCID 178418390, Verbindung
Katalysator
HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 3-[3-[4-(7-methylimidazo[1,2-a]-pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylate (926 mg), 10% palladium carbon (139 mg), dichloromethane (50 ml) and methanol (50 ml) was hydrogenated under one atmospheric pressure of hydrogen at ambient temperature for 2.5 hours. After filtration, acetic acid (1 ml) was added to the filtrate containing ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl-1-piperazinyl]-6-aminophenyl]propionate and 6-[4-(7-methylimidazo[1,2-a]-pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone and evaporated in vacuo. The residue was dissolved in chloroform (30 ml) and washed with saturated aqueous solution of sodium hydrogene carbonate. The extract was dried over magnesium sulfate and concentrated. The residue was crystallized from ethanol to give 6-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(lH)-quinolinone (612 mg).

Aufarbeitung

  1. filtrationAfter filtration, acetic acid (1 ml)
  2. additionwas added to the filtrate
  3. additioncontaining ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl-1-piperazinyl]-6-aminophenyl]propionate and 6-[4-(7-methylimidazo[1,2-a]-pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in chloroform (30 ml)
  6. washwashed with saturated aqueous solution of sodium hydrogene carbonate
  7. dry with materialThe extract was dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0c42e2c52dbd4abc8b3b4f979b59904e
Quelldatensatz
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04988698

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