Aminoacetonitrile sulfate (1:1) → HCID 178420611, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (140 mg, 2 mmol) in H2O (1 ml) was added to a stirred solution of 3-imidazo[1,2-a]pyridin-3-yl-phenylamine (420 mg, 2 mmol) in 2N HCl (4 ml) such that the internal temperature <5° C. After complete addition the reaction was stirred 15 minutes at this temperature before the addition of aminoacetonitrile hydrogen sulphate (310 mg, 2 mmol) in H2O (1 ml) [internal temperature maintained <5° C.]. After 1 hour NaOAc (7 g) was added. The mixture was stirred for 1 hour with ice bath cooling, then the solid was collected by filtration. This material was taken up in EtOH directly (˜10 ml). This solution was stirred and heated at 90° C. for 18 hours under N2. After cooling to RT the volatiles were removed in vacuo and the residue was purified by chromatography on silica (100% CH2Cl2→4% 2M NH3-MeOH/CH2Cl2) to give the title compound (219 mg, solid). MS: [M+H]+ 277

Provenance & Evidence