Hydrochloric Acid → HCID 178426582, Verbindung

HRID 16692

Reaktionsgleichung

Reaktionsgleichung von HRID 16692
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C[Al](C)C.CCCCCC.[O:19]=[C:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]([NH:34][C:35]2[C:39]3=[N:40][CH:41]=[CH:42][CH:43]=[C:38]3[O:37][C:36]=2[C:44](OC)=[O:45])=[O:33])[CH2:28][CH2:27]1.Cl.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:44]([C:36]2[O:37][C:38]3[C:39](=[N:40][CH:41]=[CH:42][CH:43]=3)[C:35]=2[NH:34][C:32]([C@H:29]2[CH2:30][CH2:31][C@H:26]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][C:20]3=[O:19])[CH2:27][CH2:28]2)=[O:33])=[O:45])=[N:3][CH:4]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 153482-Amino-5-methylpyridineHCID 516892Sodium BicarbonateHCID 86584505Trimethylaluminum hexaneHCID 178499199HCID 178499199, Verbindung

Produkt 1

HCID 178426582HCID 178426582, VerbindungAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Amino-5-methylpyridine (81 mg) is dissolved in chloroform (5 ml). After adding 0.98 M trimethyl aluminum-hexane solution (763 μl) under ice-cooling, the reaction solution is stirred under ice-cooling for 10 minutes, and then at room temperature for 0.5 hours. To the resulting reaction solution is added methyl 3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-2-carboxylate (150 mg) obtained in Reference Example 79, and the mixture is stirred at room temperature for 2 hours and at 50° C. under heating for 5 hours. To the reaction solution is added 10% hydrochloric acid (3 ml) under ice-cooling, and the mixture is stirred at room temperature for 0.5 hours. The reaction solution is then neutralized by adding saturated aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1). The resulting solid is suspended in diethyl ether, and collected by filtration to give the title compound (110 mg).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling for 10 minutes
  3. customTo the resulting reaction solution
  4. customobtained in Reference Example 79
  5. stirringthe mixture is stirred at room temperature for 2 hours and at 50° C.
  6. temperatureunder heating for 5 hours
  7. temperaturecooling
  8. stirringthe mixture is stirred at room temperature for 0.5 hours
  9. extractionextracted with chloroform
  10. washThe organic layer is washed with saturated brine
  11. dry with materialdried over sodium sulfate
  12. customthe solvent is evaporated under reduced pressure
  13. customThe residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1)
  14. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-eae17f8ebaf8493a9c5aabf38ce0cd74
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737161B2

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