Sodium Bicarbonate → HCID 68991018, Verbindung

HRID 656971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656971
[ClH:1].Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]=[CH:14][C:13]2=[O:23])[CH2:6][CH2:5]1.O=[C:25]1[CH2:30][O:29][C:28]2[CH:31]=[CH:32][C:33]([CH:35]=O)=[N:34][C:27]=2N1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.C(N(CC)CC)C.C(Cl)(Cl)Cl>[ClH:1].[ClH:1].[O:29]1[C:28]2=[CH:27][N:34]=[C:33]([CH2:35][NH:3][CH:4]3[CH2:5][CH2:6][N:7]([CH2:10][CH2:11][N:12]4[C:21]5[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=5)[N:15]=[CH:14][C:13]4=[O:23])[CH2:8][CH2:9]3)[CH:32]=[C:31]2[CH2:25][CH2:30]1

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 688175421-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride

Produkt 1

HCID 68991018HCID 68991018, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride (60 mg; 0.166 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003087098, Example 31(e))(35 mg, 0.20 mmol) in MeOH (3 ml), chloroform (3 ml) and triethylamine (0.06 ml) was heated under reflux with 3A molecular sieves overnight. It was cooled and sodium triacetoxyborohydride (0.11 g; 0.52 mmol) was added, and the mixture was stirred at rt for 7-8 h. Aqueous sodium bicarbonate solution was added to basify and the aqueous phase was extracted several times with 10% MeOH-DCM. The organic fractions were dried and evaporated. Chromatography on silica gel, eluting with 0-20% MeOH-DCM gave the free base of the title compound (68 mg, 91%).

Aufarbeitung

  1. temperatureIt was cooled
  2. extractionthe aqueous phase was extracted several times with 10% MeOH-DCM
  3. customThe organic fractions were dried
  4. customevaporated
  5. washChromatography on silica gel, eluting with 0-20% MeOH-DCM

Quellen und Nachweise

ORD-Eintrag
ord-0b9e9747144e4f8d8f32c4a28f54c613
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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