N-(4-(2-(benzyloxy)ethoxy)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2,6-difluorophenyl)acetamide → 2-[4-(5-ethoxy-6-oxo-1H-pyridin-3-yl)-2,6-difluorophenyl]-N-[4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl]acetamide

HRID 1428591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428591
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:48])[CH2:20][C:21]2[C:26]([F:27])=[CH:25][C:24]([C:28]3[CH:29]=[N:30][C:31]([O:37]CC4C=CC(OC)=CC=4)=[C:32]([O:34][CH2:35][CH3:36])[CH:33]=3)=[CH:23][C:22]=2[F:47])=[CH:14][C:13]=1[C:49]([F:52])([F:51])[F:50])C1C=CC=CC=1>CO.[Pd]>[CH2:35]([O:34][C:32]1[C:31](=[O:37])[NH:30][CH:29]=[C:28]([C:24]2[CH:25]=[C:26]([F:27])[C:21]([CH2:20][C:19]([NH:18][C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][OH:8])=[C:13]([C:49]([F:50])([F:52])[F:51])[CH:14]=3)=[O:48])=[C:22]([F:47])[CH:23]=2)[CH:33]=1)[CH3:36]

Komponenten

4

Edukt 1

HCID 90416829N-(4-(2-(benzyloxy)ethoxy)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2,6-difluorophenyl)acetamide

Produkt 1

HCID 784264712-[4-(5-ethoxy-6-oxo-1H-pyridin-3-yl)-2,6-difluorophenyl]-N-[4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl]acetamideAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of N-(4-(2-(benzyloxy)ethoxy)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2,6-difluorophenyl)acetamide (70 mg, 0.097 mmol) and Pd/C (10.31 mg, 0.097 mmol) in MeOH (10 mL) was stirred under a H2 atmosphere for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was filtered. The filtrate was concentrated to give the crude product, which was purified by preparative HPLC to yield a white solid of 2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2,6-difluorophenyl)-N-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)acetamide (7 mg, 0.014 mmol, 14.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.83 (d, J=2.4 Hz, 1H), 7.71 (d, J=6.8 Hz, 1H), 7.36 (d, J=2.0 Hz, 1H), 7.24 (dd, J=3.0, 5.4 Hz, 3H), 7.16 (d, J=9.0 Hz, 1H), 4.07-4.20 (m, 4H), 3.87 (t, J=5.0 Hz, 2H), 3.81 (s, 2H), 1.46 (t, J=7.06 Hz, 3H); ES-LCMS m/z 513.1 (M+H).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-12d3a0dd5b4c4d388d75bc8b50372f43
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937071B2

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