反应 #53401

反应方程式

Compound 33

4-[4-(2,3-Dihydroxypropyloxyl)phenyl]butylamidino-3,5-diamino-6-chloropyrazinecarboxamide Hydrochloride

methanol

p-Toluenesulfonic acid monohydrate

→

Compound 37

收率 185.6%

4-[4-(2,2 Dimethyl-[1,3]dioxolan-4 yl)methyloxyphenyl]butylamidino-3,5-diamino-6-chloropyrazinecarboxamide

收率 185.6%

溶剂

acetone

反应条件

后处理

1. 1
   其他was formed (approx. 15 mL)
2. 2
   过滤After this time, the reaction mixture was filtered
3. 3
   workup.ADDITIONsilica gel (20 mL) was added
4. 4
   其他the solvent was removed under reduced pressure
5. 5
   workup.ADDITIONThis silica gel with the reaction mixture adsorbed was added to the top of a silica gel flash chromatography column

实验过程

Compound 33 (150 mg, 0.3 mmol) was suspended in dry acetone (50 mL) then methanol was added until a clear solution was formed (approx. 15 mL). p-Toluenesulfonic acid monohydrate (25 mg) was added along with molecular sieves (5 A) and the reaction mixture was stirred for 48 h at room temperature. After this time, the reaction mixture was filtered, silica gel (20 mL) was added and the solvent was removed under reduced pressure. This silica gel with the reaction mixture adsorbed was added to the top of a silica gel flash chromatography column. Compound 37 (120 mg, 81%) was isolated by flash chromatography (silica gel, 10:1:0.1 chloroform/methanol/concentrated ammonium hydroxide) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.30 (s, 3H), 1.34 (s, 3H), 1.52 (br s, 4H), 2.56 (br s, 2H), 3.13 (br s, 2H), 3.71 (m, 1H), 3.92 (m, 2H), 4.08 (m, 1H), 4.45 (m, 1H), 6.64 (br s, 2H), 6.82 (m, 2H), 7.12 (m, 2H). APCI MS m/z=492 [C22H30ClN22H30ClN7O4+H]+.

来源