2-Cyano-2-oximinoacetamide synthesis

Yield:3849-20-5 89%

Reaction Conditions:

with acetic acid;sodium nitrite in water at 20; for 0.5 h;

Steps:

N-(2-Cyclopropylpropan-2-yl)-7-methyl-5-(pyridin-3-yl)isothiazolo j4,5-bl pyridine-3- carboxamide

To a solution of 2-cyanoacetamide (10.0 g, 0.119 mol) and sodium nitrite (10.0 g, 0.145 mol) in water (100 g, 5 mol) was added AcOH (13.3 mL, 0.234 mol) dropwise over 30 mins maintaining the temperature below 20 °C with the ice bath. The reaction mixture was then stirred overnight, gradually warming to RT. After 12 h the aqueous layer was extracted withEA (100 mL x 2). The combined organic layers were dried over Mg2SO4, and filtered. The filtrate was concentrated in vacuo to afford 2-amino-N-hydroxy-2-oxoacetimidoyl cyanide (12 g, 89%) as a white solid ‘H NMR (500 MHz, DMSO-d6) 5 14.45 (s, 1H), 7.90 (s, 1H), 7.83 (s, 1H). LC-MS m/z: 135.9 [M+Naf’. tR= 0.33 mm

References:

WO2017/192930,2017,A1 Location in patent:Paragraph 00390