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4-Methoxybenzaldehyde → HCID 11490484, Verbindung

HRID 1727039
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1727039
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2=[N:9][C:10]([N:13]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[NH:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1.[CH:37](=O)[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.CO.O>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([CH2:37][NH:1][CH2:2][CH2:3][N:4]2[C:8]3=[N:9][C:10]([N:13]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])=[CH:11][CH:12]=[C:7]3[N:6]=[C:5]2[NH:24][C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)=[CH:39][CH:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57566331HCID 57566331, Verbindung

Produkt 1

HCID 11490484HCID 11490484, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887
Methanol
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3-(2-aminoethyl)-N5,N5-bis(3-methylbutyl)-N2-(3,4,5-trimethoxyphenyl)-3H-imidazo[4,5-b]pyridine-2,5-diamine (83 mg, 1 eq) and p-anisaldehyde (25 mg, 1 eq) in dichloromethane (1.5 ml) is stirred for 6 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (2 ml) then sodium triacetoxyborohydride (70 mg, 2 eq) is added. After stirring for 0.5 hour at a temperature of approximately 20° C., dichloromethane (20 ml) and water saturated with sodium hydrogen carbonate (10 ml) are added to the mixture. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 2:8) produces the expected compound (70 mg, 68% yield).

Aufarbeitung

  1. additionare added to the mixture
  2. extractionAfter decantation and extractions
  3. washthe combined organic phases are washed with salt water
  4. dry with materialdried over Na2SO4
  5. concentrationthen concentrated under reduced pressure at 40° C
  6. customPurification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 2:8)

Quellen und Nachweise

ORD-Eintrag
ord-02defa71186e4b1ca94d0a46f10bd066
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495009B2

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