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

HRID 1182153

Reaktionsgleichung

Reaktionsgleichung von HRID 1182153
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][C@H:13]([NH2:15])[CH3:14])[CH2:8]2)=[CH:4][CH:3]=1.C1([O:24][C:25](=O)[NH:26][C:27]2[S:28][C:29]([CH2:32][CH3:33])=[N:30][N:31]=2)C=CC=CC=1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][C@H:13]([NH:15][C:25]([NH:26][C:27]3[S:28][C:29]([CH2:32][CH3:33])=[N:30][N:31]=3)=[O:24])[CH3:14])[CH2:8]2)=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 66876196Phenyl 5-ethyl-1,3,4-thiadiazol-2-ylcarbamateHCID 69409912(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propylamine

Produkt 1

HCID 101268841-{(R)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of (R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propylamine (0.145 mg, 0.569 mmol) and (5-ethyl-[1,3,4]thiadiazol-2-yl)-carbamic acid phenyl ester (0.142 mg, 0.569 mmol) in DMSO is stirred at room temperature for 4 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 recrystallised from hot ethylacetate to afford 1-{(R)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea. [M+H] 410.14.

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 recrystallised from hot ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-bde66ebe4c6e4280912343d9ba9d4257
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288537B2

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