Triethylamine → [2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]carbamic acid 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridin-7-ylmethyl ester

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Reaction Steps

In toluene (50 ml), 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid (1.11 g, 3.91 mmol) prepared in Example 7-1 and (1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridin-7-yl)methanol (870 mg, 4.30 mmol) prepared in Example 3-1 were suspended. Triethylamine (475 mg, 4.69 mmol) and then diphenylphosphoryl azide (1.18 g, 4.30 mmol) were added to the suspension, and the mixture was heated under reflux for 2 hours. Chloroform was added to the mixture, and the resulting mixture was washed with a saturated sodium bicarbonate solution. The washed mixture was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (1.34 g, 71%) as a white powder.

Provenance & Evidence