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17th June 2014 @ 05:55
Using the method optimised by Jo, and used successfully in [blog=10183]Resynthesis of N-(3-chlorophenyl)-3-(4-(difluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyrazine-5-carboxamide (TM 14-2)[/blog], TM 26-1 was obtained in 73 % yield. Purified TM 24-1 ([blog=10125]Synthesis of (5-chloro-2-methylphenyl)-6-(2-(4-(difluoromethoxy)benzylidene)hydrazinyl)pyrazine-2-carboxamide (TM 24-1)[/blog]) (200 mg, 0.46 mmol) was stirred into DCM (10 mL), phenyliodine diacetate (PIDA) (1 eq, 0.46 mmol, 148 mg) added, and the reaction mixture stirred at RT for 6 hours. The reaction mixture was washed with saturated NaHCO3 solution (15 mL), then the aqueous portion was re-extracted with DCM (5 x 10 mL), and concentrated under vacuum to give crude TM 26-1. The crude was purified by automatic column chromatography to give pure TM 26-1 as a pearlescent white solid (144 mg, 0.33 mmol, 73 %). InChIs: InChI=1S/C20H16ClF2N5O2/c1-12-2-5-14(21)8-16(12)27-19(29)17-10-24-11-18(26-17)28-25-9-13-3-6-15(7-4-13)30-20(22)23/h2-11,20H,1H3,(H,26,28)(H,27,29)/b25-9- to InChI=1S/C20H14ClF2N5O2/c1-11-2-5-13(21)8-15(11)25-19(29)16-9-24-10-17-26-27-18(28(16)17)12-3-6-14(7-4-12)30-20(22)23/h2-10,20H,1H3,(H,25,29) HIRAC: [data]11809[/data]  
Attached Files
Re: Synthesis of N-(5-chloro-2-methylphenyl)-3-(4-(difluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyrazine-5-carboxamide (TM 26-1) by Alice Williamson
17th June 2014 @ 06:28
HIRAC seen and approved. Discussed the lack of hazard information for PIDA. According to Sigma Aldrich MSDS this material is non hazardous, according to other MSDS PIDA is classed as an irritant on contact with skin, eyes, inhalation or ingestion and so will be treated as irritant.