Diisopropylethylamine → HCID 54015629, compound

Participants

Reaction Conditions

Reaction Steps

At -15° C., a solution of 63 mg (0.55 mmol) of methanesulphochloride in 6 ml of chloroform is added dropwise to a stirred solution of 95 mg (0.55 mmol) of 3-(5-indolyl)allyl alcohol and 142 mg (1.10 mmol) of N-ethyl-N,N-diisopropylamine in 6 ml of anhydrous methylene chloride and the resulting mixture is stirred for 15 hours at -5° C. It is evaporated down in vacuo at 20° C., the evaporation residue is dissolved in 3 ml of anhydrous dimethylformamide, 370 mg (2.20 mmol) of 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine are added and the mixture is stirred for 4 hours at 50° C. and for 3 hours at 70° C. The mixture is then evaporated down in vacuo, distributed between chloroform and water and the dried and filtered chloroform solution is evaporated down in vacuo. The evaporation residue is purified by triple column chromatography on neutral aluminium oxide (toluene/ethyl acetate/ethanol=4:1:0.5). Yield: 8 mg (4.5% of theory), Melting point: 60°-65° C. (foamy). Molecular peak (m/z) Calculated: 324 Found: 324

Provenance & Evidence