Phenyl 5-ethyl-1,3,4-thiadiazol-2-ylcarbamate → 1-{3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea

HRID 1182152

Reaktionsgleichung

Reaktionsgleichung von HRID 1182152
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][CH2:13][NH2:14])[CH2:8]2)=[CH:4][CH:3]=1.C1([O:23][C:24](=O)[NH:25][C:26]2[S:27][C:28]([CH2:31][CH3:32])=[N:29][N:30]=2)C=CC=CC=1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][CH2:13][NH:14][C:24]([NH:25][C:26]3[S:27][C:28]([CH2:31][CH3:32])=[N:29][N:30]=3)=[O:23])[CH2:8]2)=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 66876196Phenyl 5-ethyl-1,3,4-thiadiazol-2-ylcarbamateHCID 694091233-(3-(4-Chlorobenzyl)azetidin-1-yl)propan-1-amine

Produkt 1

HCID 101506761-{3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 3-[3-(4 chloro-benzyl)-azetidin-1-yl]-propylamine (0.100 mg, 0.418 mmol) and (5-ethyl-[1,3,4]thiadiazol-2-yl)-carbamic acid phenyl ester (0.11 mg, 0.439 mmol) in DMSO is stirred at room temperature for 18 hours then partitioned between ethylacetate and water. The organic phase is washed with brine and dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 5% methanol in DCM as eluent to afford 1-{3-[3-(4-chloro-benzyl)-azetidin-1-yl]-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea. [M+H] 394.1

Aufarbeitung

  1. customthen partitioned between ethylacetate and water
  2. washThe organic phase is washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ada1071260eb4f528c5b64d0239dc748
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288537B2

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