4-Methylmorpholine → 1,1-dimethylethyl 2,3-dihydro-2-[4-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-5-propyl-1H-imidazol-2-yl]-1H-indole-1-carboxylate

HRID 887938

Reaktionsgleichung

Reaktionsgleichung von HRID 887938
O.ON1C2C=CC=CC=2N=N1.[C:12]([C:15]1[N:16]=[C:17]([CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:18][C:19]=1[CH2:20][CH2:21][CH3:22])(O)=[O:13].Cl.[CH3:40][O:41][C:42](=[O:45])[CH2:43][NH2:44].Cl.C(C(NCCCN(C)C)=N)C.CN1CCOCC1>C(Cl)Cl.C1COCC1>[CH3:40][O:41][C:42](=[O:45])[CH2:43][NH:44][C:12]([C:15]1[N:16]=[C:17]([CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]2[C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[NH:18][C:19]=1[CH2:20][CH2:21][CH3:22])=[O:13]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 122755Glycine methyl ester hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 219140991,1-dimethylethyl 2-(4-carboxy-5-propyl-1H-imidazol-2-yl)-2,3-dihydro-1H-indole-1-carboxylateHCID 178458058HCID 178458058, Verbindung

Produkt 1

HCID 219141261,1-dimethylethyl 2,3-dihydro-2-[4-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-5-propyl-1H-imidazol-2-yl]-1H-indole-1-carboxylateAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-Hydroxybenzotriazole hydrate (0.00158 mole) was added to a solution of compound 105 (0.00079 mole) in DCM (80 ml). Glycine methylester hydrochloride (0.00103 mole), N′-(ethylcarbonimidoyl)-N,N-dimethyl-1,3 propanediamine monohydrochloride (0.00103 mole) and 4-methylmorpholine (0.00103 mole) were added. THF (25 mm) was added. The reaction was stirred at room temperature for 3 days. The mixture was extracted with water. The organic phase was washed with saturated NaHCO3, 2N citric acid, saturated NaHCO3, dried over MgSO4, filtered, and concentrated, yielding 0.20 g of 1,1-dimethylethyl 2,3-dihydro-2-[4-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-5-propyl-1H-imidazol-2-yl]-1H-indole-1-carboxylate (compound 109).

Aufarbeitung

  1. extractionThe mixture was extracted with water
  2. washThe organic phase was washed with saturated NaHCO3, 2N citric acid, saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-56ced560205c47f89e8341713f3b27c0
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247432B2

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