Реакция #168374

Уравнение реакции

4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aS,7aS)-3-oxooctahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile

sodium hydride

iodomethane

→

4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aS,7aS)-4-methyl-3-oxooctahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеquenched via the addition of saturated aqueous ammonium chloride
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   СушкаThe organic layer was dried over magnesium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe resulting residue was purified via silica gel chromatography (0-20% MeOH/DCM)

Методика

4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aS,7aS)-3-oxooctahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (282 mg, 0.559 mmol) was taken up in DMF (5595 μl), and sodium hydride (22.38 mg, 0.559 mmol) and iodomethane (87 μl, 1.399 mmol) were added. The mixture was stirred for 1 hour, quenched via the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography (0-20% MeOH/DCM) to afford 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aS,7aS)-4-methyl-3-oxooctahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile as a brown foam. MS ESI calc'd. for C28H32ClN7O [M+H]+ 518. found 518.

Источник