Triethylamine hydrochloride → HCID 178521718, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (178 mg, 2.73 mmol) and triethylamine hydrochloride (356 mg, 2.59 mmol) were added to 2-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 27; 300 mg, 0.78 mmol) in 1-methyl-2-pyrrolidinone (7 mL) and then heated at 150° C. for 3 hours. On cooling the mixture was diluted with EtOAc (100 mL) and washed with H2O (50 mL). The aqueous layer was acidified with citric acid and extracted with MeOH:DCM (1:19) and the combined organics dried (MgSO4), filtered and evaporated. The residue was purified by applying the material to a 10 g Isolute NH2 column in MeOH:DCM (1:9) (10 mL) and eluting with MeOH:DCM (1:9) (6×10 mL). The column was eluted with MeOH: 2M HCl in Et2O:DCM (5:4:45) (6×10 mL) and the relevant fractions evaporated to afford the title product (246 mg, 74%) as pale pink powder.

Provenance & Evidence