HCID 86727440, compound → HCID 86727439, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-(1-benzhydryl-3-methyl-azetidin-3-yloxy)-4-methyl-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.031 g, 0.046 mmol) and Pd(OH)2/C (10%, 0.030 g) in EtOH (10 mL) was stirred at 50° C. under an atmosphere of H2 (50 psi) overnight. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was evaporated in vacuo to give 4-methyl-6-(3-methyl-azetidin-3-yloxy)-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.021 g crude) as an oil, which was used directly without purification. To a solution of 4-methyl-6-(3-methyl-azetidin-3-yloxy)-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.021 g, 0.042 mmol) in DCM (3 mL) was added TFA (1 mL). The reaction was stirred at ambient temperature for 1.5 h then the solvent was removed in vacuo and the residue was diluted with dioxane (1 mL). Aqueous ammonium hydroxide (25%, 1 mL) was added and the reaction mixture was stirred at ambient temperature for 1.5 h. The solvent was removed in vacuo and the residue was purified by preparative HPLC (Table 3, Method 15) to give 4-methyl-6-(3-methyl-azetidin-3-yloxy)-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (0.0039 g, 25%). LC/MS (Table 1, Method 5) Rt=2.088 min; MS m/z: 371 [M+H]+.

Provenance & Evidence