HCID 53434400, compound → 8-[2-(3-Fluoro-4-trifluoromethyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine

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Reaction Steps

According to the general procedure (GP10), microwave-assisted Pictet-Spengler reaction (60 W; 140° C.; 6.5 bars; 10 min.) between 2-(4-iodo-2-methyl-imidazol-1-yl)-ethylamine (51.840 mmol) and 3-(3-fluoro-4-trifluoromethyl-phenyl)-propionaldehyde (13.125 g; 59.616 mmol) afforded 8-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. LC-MS: tR=0.76 min.; [M+H]+=453.93 g/mol. Subsequent protection of the secondary amine, and purification by FC (DCM/MeOH=20/1) allowed the isolation of the pure product 8-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a pale yellow solid (15.450 g; 54%). LC-MS: tR=0.97 min.; [M+H]+=554.84 g/mol.

Provenance & Evidence