Toluene → HCID 57786794, compound

Temperature

0 °C

To 6-Bromo-imidazo[1,2-a]pyridin-8-ylamine (1.045 g, 4.93 mmol) in THF (100 mL) was added diisopropylethylamine (1.7 mL, 2.5 eq), and the resulting mixture was cooled to 0° C. With stirring, a solution of 20% phosgene in toluene (3.11 mL, 1.2 eq) was added and the resulting mixture was stirred at 0° C. for 20 minutes. Next, a 2.0M solution of methylamine in THF (24.6 mL, 10 eq) was added and the resulting mixture was stirred from 0° C. to room temperature overnight. Then next day, the solvent was removed under reduced pressure at 55° C., and ethyl acetate (175 mL) and water (50 mL) were added. The resulting mixture was stirred vigorously for 10 minutes and then the layers were separated. The organic layer was dried over magnesium sulfate, filtered and concentrated to give 1-(6-Bromo-imidazo[1,2-a]pyridin-8-yl)-3-methyl-urea as an off-white foamy powder (1.074 g).

1. stirringthe resulting mixture was stirred at 0° C. for 20 minutes
2. stirringthe resulting mixture was stirred from 0° C. to room temperature overnight
3. customThen next day, the solvent was removed under reduced pressure at 55° C.
4. additionethyl acetate (175 mL) and water (50 mL) were added
5. stirringThe resulting mixture was stirred vigorously for 10 minutes
6. customthe layers were separated
7. dry with materialThe organic layer was dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-0f43d787fe4940ce97c181162b00837d

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426441B2