Reaktion #2128182

Reaktionsgleichung

(R)-6-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole

pyrimidin-4(3H)-one

(1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine

→

title compound

3-[2-((R)-3-piperidin-1-yl-pyrrolidin-1-yl)-benzothiazol-6-yl]-3H-pyrimidin-4-one

Lösungsmittel

pyridine

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried with MgSO4
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue obtained
6. 6
   Sonstigewas chromatographed on silica gel column
7. 7
   Wascheneluting with 3% (9:1 methanol:concentrated NH4OH) in dichloromethane

Vorschrift

A solution of (R)-6-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole (Example 14, 80 mg, 0.218 mmol), pyrimidin-4(3H)-one (31.5 mg, 0.328 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (31.1 mg, 0.218 mmol), copper (27.8 mg, 0.437 mmol) and copper(I) iodide (8.32 mg, 0.044 mmol) in pyridine (3 ml) was heated in a microwave reactor to 200° C. for 30 minutes. The mixture was diluted with ether (20 mL) and washed with water, a small amount of aqueous NH4OH and brine. The organic layer was separated and dried with MgSO4 and concentrated under reduced pressure. The residue obtained was chromatographed on silica gel column eluting with 3% (9:1 methanol:concentrated NH4OH) in dichloromethane to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.43-1.52 (m, 2H), 1.58-1.69 (m, 4H), 1.94-2.11 (m, 1H), 2.25-2.37 (m, 1H), 2.39-2.58 (m, 4H), 2.96-3.09 (m, 1H), 3.40-3.63 (m, 2H), 3.72-3.92 (m, 2H), 6.56 (d, J=6.74 Hz, 1H), 7.22 (dd, J=8.72, 2.38 Hz, 1H), 7.62 (d, J=2.38 Hz, 1H), 7.65 (d, J=8.33 Hz, 1H), 7.94 (d, J=6.74 Hz, 1H), 8.20 (s, 1H); MS (DCI/NH3) m/z 382 (M+H)+.

Quelle