3,5-Dimethylisoxazole-4-isocyanate → 2-(1-{4-[3-(3,5-Dimethyl-isoxazol-4-yl)-ureido]-2-fluoro-phenyl}-piperidin-4-yl)-N,N-diethyl-2-phenyl-acetamide

HRID 1927593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927593
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[C:4]([F:28])[CH:3]=1.[N:29]([C:32]1[C:33]([CH3:38])=[N:34][O:35][C:36]=1[CH3:37])=[C:30]=[O:31]>ClCCCl>[CH3:38][C:33]1[C:32]([NH:29][C:30](=[O:31])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][CH:11]([CH:14]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])[CH2:10][CH2:9]3)=[C:4]([F:28])[CH:3]=2)=[C:36]([CH3:37])[O:35][N:34]=1

Komponenten

4

Edukt 2

HCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 693036392-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-N,N-diethyl-2-phenyl-acetamide

Produkt 1

HCID 166670902-(1-{4-[3-(3,5-Dimethyl-isoxazol-4-yl)-ureido]-2-fluoro-phenyl}-piperidin-4-yl)-N,N-diethyl-2-phenyl-acetamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-N,N-diethyl-2-phenyl-acetamide (0.30 mmol) and 4-isocyanato-3,5-dimethyl-isoxazole (1.0 mmol) in DCE (10 mL) was stirred at rt for 16 h. The precipitate that had formed was collected by filtration and dried under vacuum to give the title compound (78 mg, 50%). MS (ESI): mass calcd. for C29H36FN5O3, 521.28; m/z found, 522.4 [M+H]+. 1H NMR (CDCl3): 7.95-7.75 (br s, 1H), 7.40-7.20 (m, 5H), 7.30-6.90 (br s, 1H), 6.80-6.70 (m, 2H), 3.60-3.10 (m, 7H), 2.45-2.35 (m, 2H), 2.28 (s, 3H), 2.20-2.10 (m, 4H), 2.00-1.90 (m, 1H), 1.52-1.40 (m, 1H), 1.35-1.20 (m, 2H), 1.18-1.03 (m, 6H).

Aufarbeitung

  1. customThe precipitate that had formed
  2. filtrationwas collected by filtration
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a1ae2e4675454e7db9ec1931b402c7b7
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183239B2

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