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A solution of N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxybenzamide (1 gram, 2.62 mmol) in phosphoryl chloride (15 milliliters, 161 mmol) and N, N-dimethylaniline (0.75 milliliters) was refluxed under nitrogen for 20 hours. The mixture was cooled to room temperature, volatiles removed in-vacuo, and the brown residue azeotroped with toluene (3×20 milliliters). The crude imino chloride was dissolved in toluene (15 milliliters), an excess of benzylamine (2.57 milliliters, 23.58 mmol) was added in one portion and the mixture refluxed, under nitrogen, for 4 hours. The mixture was cooled to room temperature, volatiles removed in-vacuo, and the residue dissolved in chloroform (100 milliliters) and washed with water (2×50 milliliters). The combined organics were dried (Na2SO4) and volatiles removed in-vacuo to yield a white solid. The mixture was purified by flash chromatography (SiO2 ; ethyl acetate: hexane (1:9), followed by ethyl acetate: hexane (1:4)) to yield the title compound (624 milligrams, 50 %) as a white crystalline solid, m.p. 129°-133° C.

1. customvolatiles removed in-vacuo
2. customthe brown residue azeotroped with toluene (3×20 milliliters)
3. dissolutionThe crude imino chloride was dissolved in toluene (15 milliliters)
4. temperaturethe mixture refluxed, under nitrogen, for 4 hours
5. temperatureThe mixture was cooled to room temperature
6. customvolatiles removed in-vacuo
7. dissolutionthe residue dissolved in chloroform (100 milliliters)
8. washwashed with water (2×50 milliliters)
9. dry with materialThe combined organics were dried (Na2SO4)
10. customvolatiles removed in-vacuo
11. customto yield a white solid
12. customThe mixture was purified by flash chromatography (SiO2 ; ethyl acetate: hexane (1:9), followed by ethyl acetate: hexane (1:4))