反应 #48882

反应方程式

1-Chloro-N,N,2-trimethyl-1-propenylamine

3-[4-(azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid

2-Amino-5-methylpyrazine

pyridine

→

desired compound

收率 12.4%

3-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-pyrazin-2-ylbenzamide

收率 12.4%

溶剂

DCM

反应条件

后处理

1. 1
   workup.STIRRINGthe reaction stirred for a further 30 mins
2. 2
   其他The solvent was removed in vacuo
3. 3
   workup.ADDITIONWater (10 mL) was added
4. 4
   萃取the mixture extracted with ethyl acetate (2×10 mL)
5. 5
   洗涤washed with 1N citric acid, water (10 mL) and brine (10 mL)
6. 6
   干燥dried (MgSO4)
7. 7
   过滤filtered
8. 8
   其他evaporated in vacuo
9. 9
   其他to give the crude product which
10. 10
    其他was chromatographed on silica
11. 11
    洗涤eluting with a gradient of 50-100% ethyl acetate in isohexane

实验过程

1-Chloro-N,N,2-trimethyl-1-propenylamine (0.073 mL, 0.55 mmol) was added to a solution of 3-[4-(azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid (260 mg, 0.5 mmol) in DCM (10 mL) and stirred at RT for 1 hour. 2-Amino-5-methylpyrazine (95 mg, 1 mmol) and pyridine (0.081 mL, 1.0 mmol) were added and the reaction stirred for a further 30 mins. The solvent was removed in vacuo. Water (10 mL) was added and the mixture extracted with ethyl acetate (2×10 mL). The extracts were combined and washed with 1N citric acid, water (10 mL) and brine (10 mL), dried (MgSO4), filtered, and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (37 mg).

来源