Reaktion #1017373

Reaktionsgleichung

Dioxane

4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carbonitrile

azidotributyltin

HCl

→

title compound

Ausbeute 104.5%

N-(3-(piperidin-1-yl)propyl)-7-(2H-tetrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine

Ausbeute 104.5%

Lösungsmittel

(trifluoromethyl)benzene

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a tan suspension
2. 2
   EinengenThe mixture was concentrated to dryness and MeOH (3 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   Sonstigeto get a yellow solution
5. 5
   SonstigeThe solid obtained
6. 6
   Sonstigewas collected on a Buchner
7. 7
   WaschenThe cake was washed with diethyl ether (3×1 mL) and with Hexane (3×1 mL)
8. 8
   Sonstigethe solid dried at 30° C. under high vacuum until constant weight

Vorschrift

In a 2-5 mL microwave vial was added 4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carbonitrile (47.5 mg, 0.142 mmol) and azidotributyltin (409 μl, 1.491 mmol) in (trifluoromethyl)benzene (2 mL) to give a tan suspension. The vial was placed in the microwave and heated to 180° C. for 30 minutes. The mixture was concentrated to dryness and MeOH (3 mL) followed by HCl 4M in Dioxane (1.07 mL, 4.26 mmol) was added to get a yellow solution. To the resulting solution was added diethyl ether (3 mL) Stirred at 20° C. for 16 hours. The solid obtained was collected on a Buchner. The cake was washed with diethyl ether (3×1 mL) and with Hexane (3×1 mL) and the solid dried at 30° C. under high vacuum until constant weight to afford 56 mg of the title compound as the HCl salt. LCMS m/z 378.2 (M+H)+, retention time (on analytical HPLC)=1.30 minutes.

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