Sodium Bicarbonate → HCID 178483849, Verbindung

HRID 16686

Reaktionsgleichung

Reaktionsgleichung von HRID 16686
Cl.Cl.Cl.[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([C:14]2[O:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[NH:23][C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([NH:32][CH3:33])[CH2:28][CH2:27]2)=[O:25])=[O:13])=[N:9][CH:10]=1.[C:34]([O:38][C:39](CC(N)C=O)=[O:40])([CH3:37])([CH3:36])[CH3:35].C(OC(OCC)[CH2:50][CH2:51][NH2:52])C.[C:56](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([C:14]2[O:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[NH:23][C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([N:32]([CH3:56])[CH2:33][CH2:50][CH2:51][NH:52][C:39](=[O:40])[O:38][C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:28][CH2:27]2)=[O:25])=[O:13])=[N:9][CH:10]=1

Komponenten

8

Edukt 5

HCID 516892Sodium BicarbonateHCID 5210291-Amino-3,3-diethoxypropaneHCID 5049666Sodium triacetoxyborohydrideHCID 194345963-t-Butoxycarbonyl-aminopropanalHCID 178484811HCID 178484811, Verbindung

Produkt 1

HCID 178483849HCID 178483849, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

N-(5-Chloropyridin-2-yl)-3-({[trans-4-(methylamino)-cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-2-carboxamide trihydrochloride (300 mg) obtained in Example 119 is suspended in chloroform (7 ml). To the suspension are added 3-t-butoxycarbonyl-aminopropanal (208 mg), which can be prepared from 3-aminopropionaldehyde diethyl acetal in two steps according to the method described in a literature (Synthesis, 1994, 37) and triethylamine (334 μl) under ice-cooling, and the mixture is stirred for a few minutes. After addition of sodium triacetoxy borohydride (190 mg), the reaction solution is warmed to room temperature and stirred for 2 hours. To the reaction solution is poured saturated aqueous sodium hydrogen carbonate solution under ice-cooling, and the mixture is extracted with chloroform. The organic layer is washed successively with water and saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=20/1) to give the title compound (291 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringstirred for 2 hours
  3. temperaturecooling
  4. extractionthe mixture is extracted with chloroform
  5. washThe organic layer is washed successively with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-ac3e7add2f9e43c8bde1cac7e0d86eba
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737161B2

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