HCID 11776206, Verbindung → 2-{2-[3-(3-Methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidin-1-ylmethyl}-pyridine

HRID 1791367

Reaktionsgleichung

Reaktionsgleichung von HRID 1791367
CO[C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[O:4].O[NH:19][C:20](=[NH:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.ClCCl>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([C:20]2[N:19]=[C:3]([CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][N:6]3[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[O:4][N:29]=2)[CH:26]=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 11776206HCID 11776206, VerbindungHCID 23676156Sodium t-butoxideHCID 178490399HCID 178490399, Verbindung

Produkt 1

HCID 117254412-{2-[3-(3-Methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidin-1-ylmethyl}-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Pyridin-2-ylmethyl-piperidine-2-carboxylic acid methyl ester (50 mg, 0.213 mmol) was mixed with N-hydroxy-3-methoxy-benzamidine (29 mg, 0.174 mmol) and sodium tert-butoxide (19 mg, 0.20 mmol) in toluene (0.5 mL) in a sealed vial at 130° C. for 10 min. The reaction mixture was cooled down and diluted with dichloromethane, washed with water. The title compound was purified by silica gel colomn chromatography with 20˜30% ethyl acetate in hexanes to give a colorless oil, 20 mg (32.7%). 1H NMR (CDCl3), δ(ppm): 8.50 (d, 1H), 7.66 (m, 3H), 7.47 (d, 1H), 7.38 (t, 1H), 7.13 (dd, 1H), 7.03 (dd, 1H), 4.11 (t, 1H), 3.88 (s, 3H), 3.73 (dd, 2H), 3.04 (m, 1H), 2.42 (m, 1H), 2.03 (m, 2H), 1.46-1.90 (m, 4H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down
  2. washwashed with water
  3. customThe title compound was purified by silica gel colomn chromatography with 20˜30% ethyl acetate in hexanes
  4. customto give a colorless oil, 20 mg (32.7%)

Quellen und Nachweise

ORD-Eintrag
ord-5aa70eb55f574960b7a7ce073d20565d
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074809B2

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