Reaktion #2305686

Reaktionsgleichung

3,4-(ethylenedioxy)phenacyl bromide

(3-morpholin-4-yl-propyl)-thiourea

N,N-diisopropylethylamine

thiophene-2-carbonyl chloride

→

title compound

Ausbeute 50.9%

N-(4-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)thiazol-2-yl)-N-(3-morpholinopropyl)thiophene-2-carboxamide

Ausbeute 50.9%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 10 min
3. 3
   Einengenconcentrated in vacuo
4. 4
   TemperaturThe reaction mixture was maintained at room temperature overnight
5. 5
   Einengenconcentrated in vacuo
6. 6
   workup.DISSOLUTIONThe resulting residue was dissolved in DMSO (1.5 mL)
7. 7
   Sonstigesubjected to HPLC purification (Method Y)
8. 8
   workup.DISSOLUTIONThe resulting free amine was dissolved in MeOH (1 mL)
9. 9
   workup.ADDITION1M HCl/ether (50 mL) was added
10. 10
    FiltrationThe precipitate was filtered
11. 11
    Sonstigedried in vacuo

Vorschrift

A mixture of 3,4-(ethylenedioxy)phenacyl bromide (77 mg, 0.3 mmol) and (3-morpholin-4-yl-propyl)-thiourea (61 mg, 0.3 mmol) in dry ethanol (3 mL) was heated at reflux for 10 min, cooled to room temperature, and concentrated in vacuo. The resulting residue was suspended in dichloromethane (3 mL) followed by the addition of N,N-diisopropylethylamine (105 μL, 0.6 mmol) and thiophene-2-carbonyl chloride (34 μL, 0.32 mmol). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (1.5 mL) and subjected to HPLC purification (Method Y). The resulting free amine was dissolved in MeOH (1 mL) and 1M HCl/ether (50 mL) was added. The precipitate was filtered and dried in vacuo to provide the title compound (72 mg) as an off-white solid as the hydrochloride salt. LC/MS (ESI) m/z 472.3 [M+H]. HPLC retention time (Method A)=2.72 min.

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