반응 #366124

반응 방정식

chloroacetaldoxime

6-(2,4-dichlorophenyl)-8-ethyl-9H-purine

3-cyclopropyl-1-propyn-3-ol

acetaldoxime

N-chlorosuccinimide

chloroacetaldoxime

chloroacetaldoxime

→

9-[1-cyclopropyl-1-(3-methyl-isoxazol-5-yl)methyl]-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine

용매

triethylamine

DMF

methylene chloride

triethylamine

반응 조건

후처리

1. 1
   추출extracting the product into diethyl ether
2. 2
   세척washing with water
3. 3
   기타) The cycloaddition reaction
4. 4
   workup.ADDITIONwere added until all the starting material
5. 5
   기타was consumed
6. 6
   기타The reaction mixture was purified
7. 7
   workup.ADDITIONby adding directly to 4 column
8. 8
   세척eluting
9. 9
   기타72 mg of a white foam was collected

실험 절차

To a stirring solution of the compound of Example 7241 (90 mg, 0.24 mmol; prepared in a manner similar to that of Example 2 using 6-(2,4-dichlorophenyl)-8-ethyl-9H-purine and 3-cyclopropyl-1-propyn-3-ol) in methylene chloride (2 mL) were added chloroacetaldoxime (25 mg, 0.27 mmol) and triethylamine (0.038 mL, 0.27 mmol). (The chloroacetaldoxime used was previously prepared by reacting equimolar amounts of acetaldoxime and N-chlorosuccinimide in DMF, then extracting the product into diethyl ether and washing with water.) The cycloaddition reaction was monitored by TLC and additional amounts of chloroacetaldoxime and triethylamine were added until all the starting material was consumed. The reaction mixture was purified by adding directly to 4 column packed with silica gel and eluting using a gradient of 100% hexane to 25% ethyl acetate in hexane. 72 mg of a white foam was collected. MS (NH3-CI) 428 (M+H+). HRMS: m/e=428.1037 (M+H+, C21H20Cl2N5O). Purity by reverse phase HPLC>97%.

출처