4-Methylmorpholine → Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 1425342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425342
CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[NH2:30][CH:31]1[CH2:34][N:33]([C:35]2[S:36][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][N:39]=2)[CH2:32]1.[Cl:45][C:46]1[N:47]=[C:48]([C:53](O)=[O:54])[NH:49][C:50]=1[CH2:51][CH3:52]>CC(N(C)C)=O.ClCCl.C(OCC)(=O)C>[Cl:45][C:46]1[N:47]=[C:48]([C:53]([NH:30][CH:31]2[CH2:34][N:33]([C:35]3[S:36][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][N:39]=3)[CH2:32]2)=[O:54])[NH:49][C:50]=1[CH2:51][CH3:52]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67548752Ethyl 2-(3-aminoazetidin-1-yl)-1,3-thiazole-5-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

Produkt 1

HCID 67548970Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-thiazole-5-carboxylateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 85741463dichloromethane N,N-dimethylacetamideLösungsmittel

Versuchsvorschrift

WSC hydrochloride (62 mg, 0.32 mmol), 1-hydroxybenzotriazole (36 mg, 0.27 mmol) and N-methylmorpholine (0.06 mL, 0.54 mmol) were added to a mixed solution of ethyl 2-(3-aminoazetidin-1-yl)-1,3-thiazole-5-carboxylate obtained in Example (217b) (61 mg, 0.27 mmol) and 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (47 mg, 0.27 mmol) in DMA/dichloromethane (2 mL/2 mL), and the mixture was stirred at room temperature for 19 hours. The reaction solution was diluted with ethyl acetate, and then the mixture was washed with brine and dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=20/1) to obtain 66 mg of the title compound as a white solid (64%).

Aufarbeitung

  1. washthe mixture was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-58278fcc1a9a4447a8f32cf4a0fc569a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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