Hydrazine → HCID 69670263, compound

Participants

Reaction Conditions

Reaction Steps

Methyl isocyanate (1.4 mg, 0.025 mmol) was added to a solution of 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile (10 mg, 0.025 mmol, from Step 3 of Example 199) in THF (0.5 mL) at room temperature. After 18 h at room temperature, LCMS analysis showed that the first step was complete. The mixture was concentrated. The solid residue was treated with hydrazine (40 μL, 1.274 mmol) and N,N-dimethylacetamide (500 μL). The mixture was heated to 120° C. for 6 h and at 150° C. for 1 h. The crude material was diluted with water (0.5 mL) and methanol (1 mL) and purified by reverse phase HPLC (Sunfire S10 30×250 mm column), eluting with 40-70% solvent B (10% methanol-90% water-0.1% TFA) in solvent A (90% methanol-10% water-0.1% TFA). Example 203 was obtained as yellow solid (2.6 mg, 15% yield).

Provenance & Evidence