Dimethylformamide → HCID 178482762, compound

To a solution of 4-(2-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)ethyl)aniline (100 mg, 0.192 mmol) in DMF (4 mL) was added NaH (15 mg, 0.575 mmol) followed by methyl iodide (24 μL, 0.383 mmol). The reaction was stirred at room temperature for 20 h and quenched with water. Methanol (3 mL) and acetic acid (1 mL) were added to the reaction mixture and heated at 80° C. for 2 h. The mixture was poured into water (10 mL) and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water (10 mL), brine (10 mL), dried and concentrated. The crude product was purified by flash column chromatography (silica gel, 3%-7% MeOH/DCM as eluent) to afford the desired product as a gel (32 mg, 0.104 mmol, 54%). 1H NMR: 3.02 (s, 6H), 3.16 (t, 2H, J=6.4 Hz), 4.39 (t, 2H, J=6.4 Hz), 6.99 (t, 4H, J=7.8 Hz), 7.18-7.24 (m, 2H), 7.35 (d, 2H, J=10.8 Hz), 7.69 (s, 1H), 7.70 (d, 1H, J=7.2 Hz).

1. customquenched with water
2. additionMethanol (3 mL) and acetic acid (1 mL) were added to the reaction mixture
3. temperatureheated at 80° C. for 2 h
4. additionThe mixture was poured into water (10 mL)
5. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
6. washThe combined organic layers were washed with water (10 mL), brine (10 mL)
7. customdried
8. concentrationconcentrated
9. customThe crude product was purified by flash column chromatography (silica gel, 3%-7% MeOH/DCM as eluent)

ORD record

ord-9502d256262a41fb97ee66fa5d9b4b45

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722720B2