Triethylamine → HCID 66888934, compound

Participants

Reaction Conditions

Reaction Steps

240 microlitres (2.78 mmol) of oxalyl chloride are added, dropwise at 0° C., to a solution of 0.4 g (1.39 mmol) of 5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid, prepared in step 1.1, in 10 mL of dichloromethane and 0.5 mL of dimethylformamide. The mixture is stirred for 15 minutes at 0° C. and then for 1 hour at 20° C. After this time, a further 120 microlitres (1.39 mmol) of oxalyl chloride are added and stirring is continued for 30 minutes at 20° C. The reaction mixture is then concentrated under reduced pressure and taken up in 5 mL of tetrahydrofuran. 219 microlitres of triethylamine and then a solution of 0.44 g (1.67 mmol) of (6-amino-thiazolo[5,4-b]pyrid-2-yl)methyl 2,2-dimethylpropanoate, prepared in step 4.2, in 10 mL of tetrahydrofuran are added, under an inert atmosphere. The reaction mixture is stirred for 15 hours at 20° C. and for 1 hour at 40° C., and then concentrated under reduced pressure and taken up in 100 mL of water. The aqueous phase is extracted three times with 50 mL of ethyl acetate. The organic phases are combined, washed successively with 50 mL of saturated sodium hydrogen carbonate solution and with 50 mL of saturated sodium chloride solution, and then dried over sodium sulfate and concentrated under reduced pressure. The product thus obtained is purified on a column of alumina, eluting with dichloromethane. 0.15 g of the expected product is thus isolated.

Provenance & Evidence