반응 #168412
ord-796693684dfb49a3b32f0bc75f15ea06
반응 방정식
반응물
시약
용매
반응 조건
후처리
- 1기타The reaction mixture was then quenched with a saturated aqueous solution of NaHCO3 (5 mL)
- 2추출extracted with CH2Cl2 (2×15 mL)
- 3세척The combined organic layers were washed with brine (10 mL)
- 4건조dried over anhydrous Na2SO4
- 5여과filtered
- 6농축concentrated
- 7기타Purification of the resulting residue on a silica gel column (0 to 100% ethyl acetate/hexanes)
실험 절차
To a solution of 4-(5-chloropyridin-3-yl)-2-[(1RS)-1-(3-fluoropyridin-2-yl)-1-hydroxyethyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (156 mg, 0.31 mmol) in CH2Cl2 (10.0 mL) at −40° C. under a nitrogen atmosphere was added DAST (0.08 mL, 0.22 mmol), and the resulting solution was stirred at this temperature for 1 hour. The reaction mixture was then quenched with a saturated aqueous solution of NaHCO3 (5 mL) and extracted with CH2Cl2 (2×15 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated. Purification of the resulting residue on a silica gel column (0 to 100% ethyl acetate/hexanes) afforded 4-(5-chloropyridin-3-yl)-2-[(1RS)-1-fluoro-1-(3-fluoropyridin-2-yl)ethyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS APCl calcd. for C27H25ClF2N6 [M+H]+ 507. found 507. The two enantiomers were separated on a chiralpak-AD column (15% IPA/heptane) to afford faster eluting Enantiomer A and slower eluting Enantiomer B.