2-Aminothiazole → HCID 57433635, compound

To a mixture of 2-aminothiazole (0.976 g, 9.74 mmol) and 2-bromo-1-(4-fluoro-3-methoxy-phenyl)-ethanone (2.4 g, 9.74 mmol) was added absolute ethanol (100 ml). The reaction was allowed to reflux with vigorous stirring for 18 hours (checked by HPLC). The reaction mixture was reduced to half its original volume in vacuo. The remaining liquid was poured onto ice and the solution made basic by the addition of ammonium hydroxide solution (30%), until pH is 8. The mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with water (100 ml) and saturated aqueous sodium chloride solution (100 ml). The organic phase was dried with sodium sulfate, filtered and concentrated in vacuo, to give an orange solid. Purification by flash chromatography (gradient 25%-50% ethyl actetate in hexanes) afforded the title product as a pale yellow solid (1.59 g, 66%). 400 MHz 1H NMR (DMSO-d6) δ 8.26 (s, 1H), 7.95 (d, J=2.3 Hz, 1H), 7.61 (dd, J=8.6, 2.0 Hz, 1H), 7.39 (ddd, J=8.2, 4.3, 2.0 Hz, 1H); 7.28 (d, J=4.7 Hz, 1H), 7.22 (dd, J=11.3, 8.2 Hz, 1H), 3.91 (s, 3H). LCMS: 249 [M+H].

1. temperatureto reflux
2. additionThe remaining liquid was poured onto ice
3. extractionThe mixture was extracted with ethyl acetate (2×100 ml)
4. washThe combined extracts were washed with water (100 ml) and saturated aqueous sodium chloride solution (100 ml)
5. dry with materialThe organic phase was dried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give an orange solid
9. customPurification by flash chromatography (gradient 25%-50% ethyl actetate in hexanes)

ORD record

ord-2497737102b64838b6c521fcd40fd95e

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501430B2