1,10-Phenanthroline → (4R)-6-(4-chlorophenyl)-1,4-dimethyl-8-(5-methyl-1,2,4-triazol-1-yl)-4,5-dihydro-[1,2,4]triazolo[3,4-d][1,5]benzodiazepine

온도

130 °C

A mixture of (R)-8-bromo-6-(4-chlorophenyl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (60 mg, 0.15 mmol), 3-methyl-1H-1,2,4-triazole (14 mg, 0.16 mmol), copper (I) iodide (6 mg, 0.03 mmol), 1,10-phenanthroline (11 mg, 0.06 mmol) and cesium carbonate (98 mg, 0.3 mmol) in dimethyl sulfoxide (3 mL) was heated at 130° C. for 30 minutes under microwave (pressure: 1.0 bar, equipment power: 150 W). The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (10 mL×3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give a crude product which was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to afford (R)-6-(4-chlorophenyl)-1,4-dimethyl-8-(5-methyl-1H-1,2,4-triazol-1-yl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (15 mg, 25%) and (R)-6-(4-chlorophenyl)-1,4-dimethyl-8-(3-methyl-1H-1,2,4-triazol-1-yl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (8 mg, 13%) as a light yellow solid.

1. washwashed with brine (10 mL×3)
2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated
5. customto give a crude product which
6. customwas purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

ORD 기록

ord-03e61344b64646148a19bfc0a91c07ab

출처 데이터셋

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09422292B2