Cyclohexanemethylamine → 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

HRID 1922210

Reaktionsgleichung

Reaktionsgleichung von HRID 1922210
CS([C:4]1[O:5][C:6]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1)=O.[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH:24]1([CH2:30][NH:31][C:4]2[O:5][C:6]3[CH:12]=[C:11]([O:13][C:14]4[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=4)[CH:10]=[CH:9][C:7]=3[N:8]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

4

Edukt 2

HCID 76688CyclohexanemethylamineHCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

Produkt 1

HCID 577255594-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide (1.40 g, 4.23 mmol, 1.0 eq) in 15 mL of THF was added cyclohexylmethanamine (955 mg, 8.46 mmol, 2.0 eq) at room temperature. The reaction mixture was stirred at that temperature for 2 hours. After the solvent was removed under reduced pressure, the residue was dissolved in 150 mL of ethyl acetate. The resulting mixture was washed with water (20 mL), brine (20 mL), then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by silica gel column eluted with ethyl acetate and hexane to give the titled compound. MH+=381.

Aufarbeitung

  1. customAfter the solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 150 mL of ethyl acetate
  3. washThe resulting mixture was washed with water (20 mL), brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give crude product, which
  8. customwas purified by silica gel column
  9. washeluted with ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-a4a54f3e0f16410f81df4789dac71e64
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173689B2

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