Formaldehyde → HCID 10070527, Verbindung

HRID 1765079

Reaktionsgleichung

Reaktionsgleichung von HRID 1765079
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15][C:16]2[C:21]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][C@H:23]3[CH3:28])=[N:20][CH:19]=[CH:18][N:17]=2)=[CH:10][CH:9]=[CH:8][N:7]=1.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.[OH-].[Na+]>ClCCCl.O>[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15][C:16]2[C:21]([N:22]3[CH2:27][CH2:26][N:25]([CH3:30])[CH2:24][C@H:23]3[CH3:28])=[N:20][CH:19]=[CH:18][N:17]=2)=[CH:10][CH:9]=[CH:8][N:7]=1

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 9870582(2R)-1-[3-(2-{[2-(2-dimethylaminoethoxy)-3-pyridinyl]oxy}ethoxy)-2-pyrazinyl]-2-methylpiperazine

Produkt 1

HCID 10070527HCID 10070527, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-{2-[{2-[2-(dimethylamino)ethoxy]pyridin-3-yl}oxy]ethoxy}-3-[(2R)-2-methylpiperazin-1-yl]pyrazine (from Example 1; 0.48 g, 1.19 mmol) in 1,2-dichloroethane (4 mL) was added sodium triacetoxyborohydride (1.3 g, 6.2 mmol) and 37% aqueous formaldehyde (0.072 g, 2.4 mmol), the slightly exothermic reaction was stirred at ambient temperature overnight. Water was added and the mixture was made basic (pH>13) by addition of 8 M NaOH. After being stirred for five minutes, the phases were separated and the aqueous phase was extracted twice with CHCl3. The combined organic phases were dried (MgSO4) and the solvent was removed under reduced pressure. The resulting oil was chromatographed on a column of silica (80 mm, i.d.=30 mm) with CHCl3/MeOH/NH4OH (95:5:0.2; 100 mL, followed by 90:10:0.2) as eluent to give 0.33 (67%) of the title compound as a colorless oil. HRMS m/z calcd for C21H32N6O3 (M)+ 416.2536. found 416.2523.

Aufarbeitung

  1. customthe slightly exothermic reaction
  2. stirringAfter being stirred for five minutes
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted twice with CHCl3
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting oil was chromatographed on a column of silica (80 mm, i.d.=30 mm) with CHCl3/MeOH/NH4OH (95:5:0.2; 100 mL, followed by 90:10:0.2) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-9c90cab5d466417cace0a24cc0155990
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226925B2

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