Hexane → 3-Amino-5-chloro-6-(2-hydroxy-ethoxy)-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acid methylester (0.250 g, 0.676 mmol) in THF (3 ml) at −78° C. is added dropwise a solution of diisobutylaluminum hydride (1.5M in toluene)(1.35 ml, 2.03 mmol). The reaction solution is stirred at −78° C. for 30 minutes, then room temperature for 1 hour. If the reaction is not complete, according to TLC (2:1 EtOAc:hexane), an additional 1.0 eq of diisobutylaluminum hydride (1.5M in toluene)(0.45 ml, 0.676 mmol) may be added. After 15 minutes, the reaction is quenched by the addition of 3 ml of a 1:1 mixture of MeOH:water. The reaction mixture is partitioned between water and EtOAc (50 ml each), and the layers are shaken and separated. The aqueous layer is extracted with 2×50 ml of EtOAc, and the combined organic layers are dried (anhydrous magnesium sulfate), filtered, and concentrated to give a yellow solid. This solid is taken up in 2:1 EtOAc:hexane, and once dissolved, a yellow precipitate is formed. The yellow solid is collected by filtration and dried in the vacuum oven at 60° C. overnight to afford the title compound as a yellow solid (0.155 g, 67%). Mass (m/z): 342.1 (M++1).

Provenance & Evidence