Nitrogen → HCID 72704327, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl carbazate (372 mg, 4.13 mmol) and p-toluenesulfonic acid monohydrate (16 mg, 0.083 mmol) in methanol (12 mL) was purged with N2 and trimethyl orthoacetate (496 mg, 4.12 mmol) was added. The mixture was stirred at 60° C. for 4 hrs and NaHCO3 (7 mg, 0.083 mmol) was added. The solid was filtered off and the filtrate was evaporated to afford an intermediate, which was mixed with 5-amino-3-methyl-2-{[3-(2-methylethyl)phenyl]oxy}-pyridine (Intermediate 26, 200 mg, 0.83 mmol) and heated to 110° C. in a vial for 5 days. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (petroleum ether/ethyl acetate from 1:1 to 1:2) to afford the title compound (30 mg) as a grey solid.

Provenance & Evidence