반응 #472830

반응 방정식

tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate

(3-oxo-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde

sodium hydrogen carbonate

sodium cyanoborohydride

→

tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(3-oxo-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)carbamate

수율 43.2%

용매

methanol

acetic acid

dichloromethane

chloroform

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hour 30 minutes
2. 2
   기타the organic layer was separated
3. 3
   세척washed sequentially with water
4. 4
   건조a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   기타The resultant residue was purified by silica gel column chromatography

실험 절차

To a solution of 48 mg of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate in 2 mL of methanol, 50 mg of (3-oxo-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde, 2.5 mL of dichloromethane and 20 μL of acetic acid were added, and the mixture was stirred at room temperature for 40 minutes. To the reaction mixture, 9.0 mg of sodium cyanoborohydride was added, and the mixture was stirred at room temperature for 1 hour 30 minutes. Thereto were added a saturated aqueous sodium hydrogen carbonate solution and chloroform, the organic layer was separated, washed sequentially with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=50:1 to obtain 35 mg of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(3-oxo-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)carbamate as a light yellow oily substance.

출처