Reaktion #1859784

Reaktionsgleichung

compound 8a

(E)-5-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-amine

methanesulfonyl chloride

→

compound 8b

Ausbeute 11.3%

(E)-N-(5-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)methanesulfonamide

Ausbeute 11.3%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesealed tube at 30° C. for 8 h
2. 2
   SonstigeThe reaction was quenched with H2O (10 mL)
3. 3
   FiltrationThe resulting solids were collected by filtration
4. 4
   SonstigeThe crude material was purified by flash column chromatography on silica gel
5. 5
   Wascheneluting with DCM/MeOH (100:1 v/v)

Vorschrift

To a solution of compound 8a (200 mg, 0.450 mmol) in pyridine (4 mL) was added methanesulfonyl chloride (150 mg, 1.32 mmol). The resulting solution was stirred in a 10 mL sealed tube at 30° C. for 8 h. The reaction was quenched with H2O (10 mL). The resulting solids were collected by filtration. The crude material was purified by flash column chromatography on silica gel, eluting with DCM/MeOH (100:1 v/v) to obtain compound 8b as a light yellow solid (26.8 mg, 11% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 10.91 (s, 1H), 8.55 (s, 1H), 8.35 (d, J=8.4 Hz, 1H), 8.23 (s, 1H), 8.12 (d, J=2.4 Hz, 1H), 8.10-7.93 (m, 2H), 7.87 (d, J=4.8 Hz, 1H), 7.83 (d, J=2.7 Hz, 1H), 7.78-7.73 (m, 1H), 7.68-7.54 (m, 2H), 7.44 (s, 1H), 7.17 (d, J=8.7 Hz, 1H), 4.40-4.20 (m, 4H), 3.85-3.75 (m, 4H), 3.39 (s, 3H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C27H25N7O3S: 528.2 (M+H). Found 528.0.

Quelle