Ethanolamine → HCID 178433946, compound

Participants

Reaction Conditions

Reaction Steps

Ethanolamine (1.5 mL; 24.9 mmol) (Aldrich) was added to a suspension of 4-amino-3-[2-methyl-5-(5-methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (68.4 mg; 0.162 mmol) (from Example 62 supra) in dimethylsulfoxide (0.5 mL). The mixture was heated in a microwave reactor at 135° C. for 90 minutes and then for 1 hour at 140° C. The crude reaction mixture was concentrated under high vacuum with heat to remove most of the ethanolamine and DMSO. The residue was diluted with water, causing a milky precipitate to drop out of solution. The solid was collected by filtration, washed with water and dried. The material was then triturated with hot methanol to give 4-amino-3-[2-methyl-5-(5-methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide as an off-white solid. (Yield 48 mg, 67.8%).

Provenance & Evidence