Triethylamine → N-pyridazin-3-yl-4-{3-[4-(2,2,2-trifluoroethoxy)phenoxy]benzylidene}piperidine-1-carboxamide

HRID 1666528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666528
[F:1][C:2]([F:26])([F:25])[CH2:3][O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=2)[CH:13]=[C:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34](=O)[O:35]C2C=CC=CC=2)[N:28]=1.C(N(CC)CC)C>CS(C)=O>[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([N:17]2[CH2:16][CH2:15][C:14](=[CH:13][C:12]3[CH:20]=[CH:21][CH:22]=[C:10]([O:9][C:8]4[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:1])([F:25])[F:26])=[CH:24][CH:23]=4)[CH:11]=3)[CH2:19][CH2:18]2)=[O:35])[N:28]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 20150036Phenyl pyridazin-3-ylcarbamateHCID 668761824-(3-(4-(2,2,2-Trifluoroethoxy)phenoxy)benzylidene)piperidine

Produkt 1

HCID 66876005N-pyridazin-3-yl-4-{3-[4-(2,2,2-trifluoroethoxy)phenoxy]benzylidene}piperidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-(4-(2,2,2-trifluoroethoxy)phenoxy)benzylidene)piperidine (40 mg, 0.110 mmol; Example 99, Step 5), phenyl pyridazin-3-ylcarbamate (24 mg, 0.110 mmol), and triethyl amine (55 mg, 0.55 mmol) in DMSO (2.5 mL) was stirred at room temperature for overnight. The reaction was quenched with water, extracted with EtOAc, dried over sodium sulfate, concentrated, and purified by column chromatography (50% acetone/hexane) to yield the title compound. (45 mg, 80%). 1H NMR (500 MHz, CDCl3): δ ppm 8.76 (s, 1H), 7.52 (s, 1H), 7.02 (m, 2H), 6.95 (m, 2H), 6.83 (m, 2H), 6.78 (s, 1H), 6.37 (s, 1H), 4.37 (m, 2H), 3.72 (s, 2H), 3.63 (s, 2H), 2.63 (s, 2H), 2.58 (s, 2H), m/z (485.1 MH+); HPLC: 98.33%.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography (50% acetone/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e6d0d8db87824689ace65453a3d3600e
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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