Reaktion #68933

Reaktionsgleichung

5-(4-(4-methoxybenzylamino)-5-aminopyridin-2-ylamino)pyrazine-2-carbonitrile

cyclopropane carboxaldehyde

sodium metabisulfite

→

title compound

Ausbeute 16.1%

5-(2-Cyclopropyl-1H-imidazo[4,5-c]pyridin-6-ylamino)pyrazine-2-carbonitrile

Ausbeute 16.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUpon cooling
2. 2
   Sonstigethe mixture was partitioned between ethyl acetate and water
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated to a light brown solid
6. 6
   SonstigeUpon completion of the reaction
7. 7
   Einengenthe mixture was concentrated

Vorschrift

A mixture of crude 5-(4-(4-methoxybenzylamino)-5-aminopyridin-2-ylamino)pyrazine-2-carbonitrile (0.083 mmol), cyclopropane carboxaldehyde (5.9 mg, 0.083 mmol) and sodium metabisulfite (16 mg, 0.083 mmol) in DMF (1 mL) was heated at 100° C. for 4 hours. Upon cooling, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4) and concentrated to a light brown solid. The solid was stirred at 65° C. with trifluoroacetic acid. Upon completion of the reaction, the mixture was concentrated. Preparative HPLC gave the title compound (3.7 mg, 16%). 1H NMR (d6-DMSO, 400 MHz) δ 12.60 (br s, 1H), 10.75 (br s, 1H), 8.80 (s, 1H), 8.75 (s, 1H), 8.50 (s, 1H), 8.10 (s, 1H), 2.10-2.20 (m, 1H), 1.00-1.20 (m, 4H). LCMS (2) Rt=1.68 min; m/z (ESI−) 276 (M−H); (ESI+) 278 (MH+).

Quelle