Diisopropylcarbodiimide → methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylate

HRID 899918

Reaktionsgleichung

Reaktionsgleichung von HRID 899918
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:13]=[C:14]=S)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N=C=NC(C)C)(C)C.[NH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=1[NH:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>O1CCCC1>[C:44]([O:43][C:41]([NH:40][CH2:39][CH2:38][CH2:37][N:36]1[C:27]2[CH:28]=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:34]=[CH:35][C:26]=2[N:25]=[C:14]1[NH:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:42])([CH3:46])([CH3:47])[CH3:45]

Komponenten

5

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 1189003,4,5-Trimethoxyphenyl isothiocyanateHCID 11962077HCID 11962077, Verbindung

Produkt 1

HCID 11962078methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3,4,5-trimethoxyphenyl isothiocyanate (6.6 g, 1.2 eq) and diisopropylcarbodiimide (9.1 g, 3 eq) are successively added to a solution of methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate (7.75 g, 1 eq) in tetrahydrofuran (130 ml). The mixture is heated under reflux for 16 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. Water (100 ml) and dichloromethane (200 ml) are added to the residue obtained. 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 8:2 to 3:7) produces the expected compound in the form of a solid which is washed with ether (4.4 g; 36% yield).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. additionWater (100 ml) and dichloromethane (200 ml) are added to the residue
  5. customobtained
  6. extractionAfter decantation and extractions
  7. washthe combined organic phases are washed with salt water
  8. dry with materialdried over Na2SO4
  9. concentrationthen concentrated under reduced pressure at 40° C
  10. customPurification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2 to 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-31b88089c3064b9eb565feac0c26a919
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07355052B2

Verknüpfte Notizen

Wird geladen…