Sodium triacetoxyborohydride → 5-Fluoro-8-{4-[4-(8-quinolinyl)-1-piperazinyl]-1-piperidinyl]quinoline

HRID 2241970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241970
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N:19]1([C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[CH:32][CH:31]=[CH:30]3)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([N:22]3[CH2:23][CH2:24][N:19]([C:25]4[CH:26]=[CH:27][CH:28]=[C:29]5[C:34]=4[N:33]=[CH:32][CH:31]=[CH:30]5)[CH2:20][CH2:21]3)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 118307868-(1-piperazinyl)QuinolineHCID 592048481-(5-Fluoroquinolin-8-yl)piperidin-4-one

Produkt 1

HCID 120041965-Fluoro-8-{4-[4-(8-quinolinyl)-1-piperazinyl]-1-piperidinyl]quinolineAusbeute 138,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 0.120 g of 1-(5-fluoro-quinolin-8-yl)-piperidin-4-one (Step 3, 0.22 g) and 8-piperazin-1-ylquinoline (Oruz, et al., J. Med. Chem. 45:4128 (2002), 0.19 g) was added of 0.19 g sodium triacetoxyborohydride and 0.1 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water and dried over magnesium sulfate. The product was filtered through 75 ml of silica gel using 100% Ethyl acetate, to give 0.30 g of the desired product. Mp: 224° C.; MS (ES) m/z (relative intensity): 442 (M++−H, 100).

Aufarbeitung

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe product was filtered through 75 ml of silica gel using 100% Ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4ef313efd6094420b4278fbfa58941dc
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671056B2

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