Cesium carbonate → 5-Chloro-2-methoxy-N-(2-(1-(3-propylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide

HRID 2043074

Reaktionsgleichung

Reaktionsgleichung von HRID 2043074
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:31]([N:34]=[C:35]=[S:36])[CH2:32][CH3:33]>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH:21][C:35]([NH:34][CH2:31][CH2:32][CH3:33])=[S:36])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 69403Propyl IsothiocyanateHCID 122820304-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide

Produkt 1

HCID 596607065-Chloro-2-methoxy-N-(2-(1-(3-propylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

376 mg (1 mmol) of 4-(2-(5-chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide and 652 mg (2 mmol) of cesium carbonate were heated in 5 ml of N-methyl-2-pyrrolidone with 0.2 ml (1.8 mmol) of n-propyl isothiocyanate at 80° C. for 10 minutes. The reaction mixture was poured onto ice/2 M hydrochloric acid, and the precipitated solid was filtered off with suction and washed with water until neutral. The crude product obtained after purification by chromatography (silica gel; toluene/ethanol/ethyl acetate 8/1/1) was crystallized from ethyl acetate. 155 mg (33%) of the title compound were obtained as a colorless solid.

Aufarbeitung

  1. additionThe reaction mixture was poured onto ice/2 M hydrochloric acid
  2. filtrationthe precipitated solid was filtered off with suction
  3. washwashed with water until neutral
  4. customThe crude product obtained
  5. customafter purification by chromatography (silica gel; toluene/ethanol/ethyl acetate 8/1/1)
  6. customwas crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-848a96a52f05480bbf711c2aae333645
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586612B2

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