3-[5-Allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide → 2,6-Difluoro-3-[4-(4-methoxy-phenyl)-5-propyl-thiazol-2-ylmethoxy]-benzamide

HRID 415586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415586
[CH2:1]([C:4]1[S:8][C:7]([CH2:9][O:10][C:11]2[C:12]([F:21])=[C:13]([C:17]([F:20])=[CH:18][CH:19]=2)[C:14]([NH2:16])=[O:15])=[N:6][C:5]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH:2]=[CH2:3]>CO>[F:21][C:12]1[C:11]([O:10][CH2:9][C:7]2[S:8][C:4]([CH2:1][CH2:2][CH3:3])=[C:5]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:6]=2)=[CH:19][CH:18]=[C:17]([F:20])[C:13]=1[C:14]([NH2:16])=[O:15]

Komponenten

3

Edukt 1

HCID 594026523-[5-Allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide

Produkt 1

HCID 594027972,6-Difluoro-3-[4-(4-methoxy-phenyl)-5-propyl-thiazol-2-ylmethoxy]-benzamideAusbeute 239 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 3-[5-allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide (0.1 g, 0.02 mmol) in 5 ml of anhydrous methanol was added dry 50 mg of dry Pd—C. The reaction mixture was stirred at 25° C. for 12 h under hydrogen atmosphere. The reaction mixture was filtered over the bed of celite. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (230-400μ) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as white solid (0.02 g, 2%). 1H NMR (DMSO-d6, 400 MHz); δ 0.92 (t, 3H, J=7.2 Hz), 1.63-1.65 (m, 2H), 2.8 (t, 2H, J=7.6 Hz (o-coupling), 3.79 (s, 3H), 5.47 (s, 2H), 7.02 (d, 2H, J=8.8 Hz (o-coupling), 7.11 (m, 1H), 7.42 (m, 1H), 7.53 (d, 2H, J=8.8 Hz (o-coupling), 7.88 (s, 1H), 8.16 (s, 1H), 8.38 (d, 1H, J=8.4 Hz (o-coupling). MS ES+ (419.14), HPLC (method 5) Rt=16.58

Aufarbeitung

  1. dry with materialdry 50 mg of dry Pd—C
  2. filtrationThe reaction mixture was filtered over the bed of celite
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was purified by column chromatography on silica (230-400μ)

Quellen und Nachweise

ORD-Eintrag
ord-e356476665af4fc3944441fc6fb2b51e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088791B2

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