Hydrochloric Acid → HCID 86679346, compound

Participants

Reaction Steps

A mixture of 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid N′-(1-methyl-1H-indol-5-ylmethyl)hydrazide (100 mg) prepared in the Step 17-1, a 37% formaldehyde solution (23 mg), pyridine borane (0.07 ml), acetic acid (2 ml) and methanol (4 ml) was stirred at a room temperature for 41 hours. To the reaction solution, 10% hydrochloric acid (0.5 ml) was added, and the resulting mixture was stirred for 20 minutes. Thereafter, the resulting mixture was neutralized with a 1-N sodium hydroxide aqueous solution. The neutralized mixture was concentrated under a reduced pressure. Then, water was added thereto, and the mixture was subjected to extraction twice with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and a saturated saline solution in order, dried over sodium sulfate, and concentrated under a reduced pressure. The concentrate was purified by a first thin-layer chromatography (chloroform:methanol=20:1) and then a second thin-layer chromatography (hexane:ethyl acetate=1:1) to give the title compound (22 mg, 21%).

Provenance & Evidence