Formaldehyde → HCID 178461560, Verbindung

HRID 1988983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988983
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]2[NH:15][C:14]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=4)[NH:18][N:17]=3)=[N:13][C:12]=2[CH:26]=1.C=O.[BH3-][C:30]#N.[Na+]>CO.C(O)(=O)C>[CH3:1][C@H:2]1[CH2:7][N:6]([CH3:30])[CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]2[NH:15][C:14]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=4)[NH:18][N:17]=3)=[N:13][C:12]=2[CH:26]=1

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178461561HCID 178461561, Verbindung

Produkt 1

HCID 178461560HCID 178461560, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

3-[6-((2S)-2-methylpiperazinyl)benzimidazol-2-yl]-6-chloro-1H-indazole (1 equivalent) is dissolved in a mixture of MeOH and acetic acid (10:1), on molecular sieves. Paraformaldehyde (10 equivalents) is added in one portion. The reaction mixture is stirred at room temperature overnight then solid NaCNBH3 is added in small portions. The reaction mixture is refluxed for 5 hours, cooled to room temperature, filtered, and concentrated under reduced pressure. The residue is dissolved in dichloromethane and washed with saturated aqueous NaHCO3. The organic solution is dried over Na2SO4, and the solvent removed under reduced afford the desired product.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialThe organic solution is dried over Na2SO4
  8. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-990681c2de7e4a09bd5374c70f4e2ebd
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642278B2

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