Dimethylformamide → 1-(Benzyloxycarbonyl)-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

HRID 337414

Reaktionsgleichung

Reaktionsgleichung von HRID 337414
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.CN(C=O)C.[NH2:29][C:30]1[S:31][C:32]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[C:33]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]([NH:29][C:30]2[S:31][C:32]([N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)=[C:33]([C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)=[O:19])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 231441582-Amino-4-(2-furyl)-5-morpholinothiazole2×

Produkt 1

HCID 231441071-(Benzyloxycarbonyl)-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Benzyloxycarbonylpiperidine-4-carboxylic acid (5.00 g, 19.0 mmol) was dissolved in dichloromethane (80 mL), and thionyl chloride (6.93 mL, 95.0 mmol) and DMF (0.15 mL, 1.90 mmol) were added thereto, followed by stirring under heating and reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in dichloromethane (2 mL). The resulting solution was added to a solution of 2-amino-4-(2-furyl)-5-morpholinothiazole (2.01 g, 8.00 mmol) in pyridine (32 mL) obtained in Step 1 of Example 29, and then N,N-dimethylaminopyridine (97.6 mg, 0.800 mmol) was added thereto, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:3) to afford the entitled Compound 43 (4.96 g, 100%).

Aufarbeitung

  1. temperatureunder heating
  2. temperaturereflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe resulting residue was dissolved in dichloromethane (2 mL)
  5. stirringby stirring at room temperature for 1 hour
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-380679c20ae54fde87e24276a7e48ec9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889718B2

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