Reaktion #1481388

Reaktionsgleichung

product

[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ylmethyl]-piperidin-4-yl-amine

8-Methyl-8-aza-bicyclo[3.2.1]oct-3-ylamine

dichloromethane

dichloromethane

Sodium borohydride

→

title compound

[2-(4-Amino-furazan-3-yl)-1-ethyl-1-H-imidazo[4,5-c]pyridin-7-ylmethyl]-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amine dihydrochloride

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred at ambient temperature for 20 hours
2. 2
   Waschenwashed water
3. 3
   Trocknendried over sodium sulphate
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel eluting with 20% ammonia in methanol/dichloromethane

Vorschrift

The product of Example 191 Step 1 (150 mg, 0.58 mmole) in 5% acetic acid and dichloromethane (5 ml) was treated with 8-Methyl-8-aza-bicyclo[3.2.1]oct-3-ylamine (179 mg, 1.2 mmole) and stirred at ambient temperature for 20 minutes. Sodium borohydride (13 mg, 0.34 mmol) was added and the reaction mixture stirred at ambient temperature for 20 hours. The product was diluted with dichloromethane, washed water followed by saturated brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 20% ammonia in methanol/dichloromethane. to afford the title compound as a free base; (34 mg, 15%) MS (ES+) m/e 396 [M+H]+. A solution of the resulting free base (34 mg, 0.08 mmol) in anhydrous methanol (1 ml) was treated with 1M hydrochloric acid in ether and stirred for 30 minutes. The resulting white precipitate was filtered and dried in vacuo to afford the title compound as a colourless hydrochloride salt; (34 mg, 92%) MS (ES+) m/e 396 [M+H]+.

Quelle