Diisopropylcarbodiimide → methyl-2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylate

HRID 1727415

Reaktionsgleichung

Reaktionsgleichung von HRID 1727415
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]=[C:12]=S)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(N=C=NC(C)C)(C)C.[NH2:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH2:36][CH2:37][N:38]([CH3:47])[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1)[C:27]([O:29][CH3:30])=[O:28]>O1CCCC1>[CH3:30][O:29][C:27]([C:26]1[CH:31]=[CH:32][C:33]2[N:34]([CH2:35][CH2:36][CH2:37][N:38]([CH3:47])[CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[C:12]([NH:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)=[N:23][C:24]=2[CH:25]=1)=[O:28]

Komponenten

5

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 1454223,5-Dimethoxyphenyl isothiocyanateHCID 69027376Methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate

Produkt 1

HCID 69027642methyl-2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3,5 dimethoxyphenylisothiocyanate (571 mg, 1 eq) and diisopropylcarbodiimide (1.35 ml, 4 eq) are added successively to a solution of methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate (1.0 g, 1 eq) in tetrahydrofuran (10 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. The residue is taken up in ethyl acetate (100 ml) and water (40 ml). After decanting and extracting, the combined organic phases are washed with salt water, dried over Na2SO4 then evaporated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: dichloromethane/methanol 99:1 to 98:2) produces the expected compound in the form of a beige foam (1.12 g; 76% yield).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. customAfter decanting
  5. extractionextracting
  6. washthe combined organic phases are washed with salt water
  7. dry with materialdried over Na2SO4
  8. customthen evaporated under reduced pressure at 40° C
  9. customPurification of the residue by flash chromatography on silica gel (eluent: dichloromethane/methanol 99:1 to 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-f1e39c8788fd45f9ac45d27ca0a27676
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495110B2

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