Diisopropylethylamine → HCID 59143372, compound

Participants

Reaction Steps

To a solution of 137.8 mg (0.8 mmol) of 5-tert-butyl-4-methyl-thiazol-2-ylamine in DCM (4 mL) were added 169.5 mg (0.8 mmol) of 2,2,2-trichloroethyl chloroformate and 0.21 mL (1.2 mmol) of N,N-diisopropylethylamine. The reaction was stirred for 18 h at room temperature. The reaction mixture was washed with saturated aqueous NaHCO3 solution and the aqueous layer was back-extracted with DCM (2×2 mL). The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in DCE (4 mL) and a solution of 443 mg (0.8 mmol) of [1,4]diazepan-1-yl-(tetrahydro-pyran-4-yl)-methanone (triple trifluoroacetic acid salt, prepared according to Method L, step 1-2) in DCE (2 mL) and 0.42 mL (2.4 mmol) of N,N-diisopropylethylamine were added. The reaction was stirred for 18 h at 80° C. The reaction mixture was washed with 10% aqueous citric acid solution (3 mL). The aqueous layer was back-extracted with DCM (2×2 mL). The combined organic extracts were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by mass-triggered preparative LCMS to afford 92.7 mg of 4-(tetrahydro-pyran-4-carbonyl)-[1,4]diazepane-1-carboxylic acid (5-tert-butyl-4-methyl-thiazol-2-yl)-amide.

Provenance & Evidence