Piperidine → 2-[3-Methoxy-4-(3-piperidin-1-yl-propoxy)-phenyl]-7-methyl-imidazo[1,2-a]pyridine

HRID 1072036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072036
Br.Cl[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]3[CH:22]=2)=[CH:9][C:8]=1[O:23][CH3:24].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[N:25]1([CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]4[CH:22]=3)=[CH:9][C:8]=2[O:23][CH3:24])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

3

Edukt 2

HCID 8082PiperidineHCID 220155982-(4'-Chloropropoxy-3'-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine hydrobromide

Produkt 1

HCID 220156112-[3-Methoxy-4-(3-piperidin-1-yl-propoxy)-phenyl]-7-methyl-imidazo[1,2-a]pyridine

Versuchsvorschrift

The product of Step C (184 mg) and piperidine (1.5 mL) were heated at 100° C. for 4 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted twice with additional ethyl acetate (10 mL) and once with dichloromethane (10 mL). The organic portions were combined, washed with brine, and evaporated. The residue was purified via silica gel chromatography (dichloromethane/2M ammonia in methanol) to give the title compound (150 mg). 1H-NMR (CD3OD) δ 8.17 (d, J=7.0 Hz, 1H), 7.93 (s, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.38 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 7.26 (s, 1H), 6.93 (d, J=8.0 Hz, 1H), 6.68 (dd, J=7.0 Hz, J=1.5 Hz, 1H), 4.00 (t, J=6.0 Hz, 2H), 3.91 (s, 3H), 2.56 (m, 3H), 2.48 (br. s, 3H), 2.38 (s, 3H), 1.98 (m, 2H), 1.60 (m, 4H), 1.47 (m, 2H)

Aufarbeitung

  1. custompartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
  2. extractionThe aqueous portion was extracted twice with additional ethyl acetate (10 mL) and once with dichloromethane (10 mL)
  3. washwashed with brine
  4. customevaporated
  5. customThe residue was purified via silica gel chromatography (dichloromethane/2M ammonia in methanol)

Quellen und Nachweise

ORD-Eintrag
ord-33d4e986684942d2b8361dcda7cc60c7
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908929B2

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